Fungicide n-[(trisubstitutedsilyl)methyl]-carboxamide derivatives

ABSTRACT

The present invention relates to fungicidal N-[(trisubstitutedsilyl)methyl]carboxamide or its thiocarboxamide derivative, their process of preparation and intermediate compounds for their preparation, their use as fungicides, particularly in the form of fungicidal compositions and methods for the control of phytopathogenic fungi of plants using these compounds or their compositions.

The present invention relates to fungicidalN-[(trisubstitutedsilyl)methyl]carboxamide or its thiocarboxamidederivative, their process of preparation and intermediate compounds fortheir preparation, their use as fungicides, particularly in the form offungicidal compositions and methods for the control of phytopathogenicfungi of plants using these compounds or their compositions.

In international patent application WO-1995/029154 certain (thio)ureasor (thio)carbamates derivatives, acting as squalene epoxidaseinhibitors, are generically embraced in a broad disclosure of numerouscompounds of the following formula:

wherein Y can represent an oxygen or a sulfur atom, X and X′ canindependently represent an oxygen atom or a substituted ornon-substituted nitrogen atom, n can be 0, R₃ can be a hydrogen atom, ahalogen atom or a C₁-C₆-alkyl group, W represents a mono ordisubstituted aminomethyl group and R₄ can represent among many othergroups, a substituted [di-C₁-C₆-alkyl(phenyl)silyl]methyl group.However, this document does not disclose compounds wherein the(thio)urea or the (thio)carbamate can be replaced by a (thio)amide.Furthermore, there is no disclosure in this document of any compoundwherein W can represent hydrogen and Rican represent a halogen atom or aC₁-C₆-alkyl group.

In international patent application WO-2007/1039615 certain fungicidalN-[(trialkylsilyl)alkyl]carboxamide derivatives are generically embracedin a broad disclosure of numerous compounds of the following formula:

wherein Het can represent a 5-membered heterocyclic ring, n can be 2 to4, R¹ can represent a hydrogen atom, a C₁-C₆-alkyl group or aC₃-C₇-cycloalkyl group, W can represent a silicon atom, X and R³ canrepresent a hydrogen atom or a C₁-C₆-alkyl group, R², R⁴, R⁵ and R⁶ canrepresent various substituents among which a C₁-C₆-alkyl group. However,this document does not disclose compounds wherein Het can be anunsaturated or partially saturated, 6-membered heterocyclyl group.Furthermore, there is no disclosure in this document of any compoundwherein one of the three substituent R⁴, R⁵ or R⁶ can be a(hetero)aromatic ring and n can be 0.

In international patent application WO-2008/003744 certain fungicidalN-[(dialkyl-2-pyridylsilyl)methyl]carboxamide derivatives aregenerically embraced in a broad disclosure of numerous compounds of thefollowing formula:

wherein A can represent a SiR⁴R⁵ group, R³ can represent a hydrogenatom, a C₁-C₆-alkyl group or a C₃-C₇-cycloalkyl group, R¹ and R² canrepresent various substituents among which a hydrogen atom or aC₁-C₆-alkyl group, and R⁴ and R⁵ can represent a C₁-C₆-alkyl group.However, this document does not disclose compounds wherein the2-pyridine moiety can be replaced by a phenyl group or any otherheterocyclyl group. Furthermore, there is no explicit disclosure in thisdocument of any compound wherein A can be a dialkylsilyl group.

In international patent application WO-2008/081011 certain fungicidalN-[(dialkyl-2-pyridylsilyl)methyl]carboxamide derivatives aregenerically embraced in a broad disclosure of numerous compounds of thefollowing formula:

wherein Het can represent a 6-membered non fused heterocyclic ring, Acan represent a SiR⁴R⁵ group, R³ can represent a hydrogen atom, aC₁-C₆-alkyl group or a C₃-C₇-cycloalkyl group, R¹ and R² can representvarious substituents among which a hydrogen atom or a C₁-C₆-alkyl group,and R⁴ and R⁵ can represent a C₁-C₆-alkyl group. However, this documentdoes not disclose compounds wherein the 2-pyridine moiety can bereplaced by a phenyl group or any other heterocyclyl group. Furthermore,there is no explicit disclosure in this document of any compound whereinA can be a dialkylsilyl group.

In international patent application WO-2010/012795 certain fungicidalN-[(dialkyl-2-phenylsilyl)ethyl]carboxamide derivatives are genericallyembraced in a broad disclosure of numerous compounds of the followingformula:

wherein A can represent a 5-membered heterocyclic ring, T can representan oxygen atom or a sulfur atom, W can represent a SiZ¹Z² group, Z⁷ canrepresent a C₃-C₇-cycloalkyl group, Z¹ and Z² can represent aC₁-C₈-alkyl group, and Z³, Z⁴, Z⁵ and Z⁶ can represent varioussubstituents among which a hydrogen atom or a C₁-C₈-alkyl group.However, this document does not disclose compounds wherein A can be aphenyl group or an unsaturated or partially saturated, 6-memberedheterocyclyl group. Furthermore, this document does not disclosecompounds wherein the SiZ¹Z² group can be linked to the(thio)carboxamide moiety by a unique methylene group or wherein Z⁷ canrepresent a hydrogen atom or a C₁-C₆-alkyl group.

It is always of high-interest in the field of agrochemicals to usepesticidal compounds more active than the compounds already known by theman ordinary skilled in the art whereby reduced amounts of compound canbe used whilst retaining equivalent efficacy.

Furthermore, the provision of new pesticidal compounds with a higherefficacy strongly reduces the risk of appearance of resistant strains inthe fungi to be treated.

We have now found a new family of compounds which show enhancedfungicidal activity over the general known family of such compounds.

Accordingly, the present invention provides aN-[(trisubstitutedsilyl)methyl]carboxamide or its thiocarboxamidederivative of formula (I)

wherein

-   -   A represents a phenyl group that can be substituted by up to        five groups R or a carbo-linked, unsaturated or partially        saturated, 6-membered heterocyclyl group that can be substituted        by up to four groups R;    -   T represents O or S;    -   n represents 0 or 1;    -   B represents a phenyl ring that can be substituted by up to 5        groups X which can be the same or different; a naphthyl ring        that can be substituted by up to 7 groups X which can be the        same or different; a thienyl ring that can be substituted by up        to 3 groups X which can be the same or different; or a        benzothiophenyl ring that can be substituted by up to 5 groups X        which can be the same or different;    -   X represents a halogen atom; nitro; cyano; isonitrile; hydroxy;        amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl; formyloxy;        formylamino; substituted or non-substituted        (hydroxyimino)-C₁-C₈-alkyl; substituted or non-substituted        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted or non-substituted        (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl; substituted or        non-substituted (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl; substituted        or non-substituted (benzyloxyimino)-C₁-C₈-alkyl; carboxy;        carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or        non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5        halogen atoms; substituted or non-substituted C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl having 1 to 5 halogen atoms; substituted        or non-substituted C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1        to 5 halogen atoms; substituted or non-substituted C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms; substituted or        non-substituted C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl        having 1 to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;        substituted or non-substituted di-C₁-C₈-alkylamino; substituted        or non-substituted C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy        having 1 to 5 halogen atoms; substituted or non-substituted        C₃-C₈-alkynyloxy; C₃-C₇-halogenoalkynyloxy having 1 to 5 halogen        atoms; substituted or non-substituted C₃-C₇-cycloalkyl;        C₃-C₇-halogenocycloalkyl having 1 to 5 halogen atoms;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₁-C₈-alkyl;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl;        substituted or non-substituted (C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl;        substituted or non-substituted tri(C₁-C₈-alkyl)silyl;        substituted or non-substituted        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; substituted or        non-substituted C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl        having 1 to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylcarbonyloxy; C₁-C₈-halogenoalkylcarbonyloxy having 1        to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylcarbonylamino; C₁-C₈-halogenoalkyl-carbonylamino        having 1 to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkyloxycarbonyloxy; C₁-C₈-halogenoalkoxycarbonyloxy        having 1 to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylcarbamoyl; substituted or non-substituted        di-C₁-C₈-alkylcarbamoyl; substituted or non-substituted        C₁-C₈-alkylaminocarbonyloxy; substituted or non-substituted        di-C₁-C₈-alkylaminocarbonyloxy; substituted or non-substituted        N—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or non-substituted        C₁-C₈-alkoxycarbamoyl; substituted or non-substituted        N—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that can be        substituted by up to 6 groups Q which can be the same or        different; C₁-C₈-arylalkyl that can be substituted by up to 6        groups Q which can be the same or different; C₂-C₈-arylalkenyl        that can be substituted by up to 6 groups Q which can be the        same or different; C₂-C₈-arylalkynyl that can be substituted by        up to 6 groups Q which can be the same or different; aryloxy        that can be substituted by up to 6 groups Q which can be the        same or different; arylsulfanyl that can be substituted by up to        6 groups Q which can be the same or different; arylamino that        can be substituted by up to 6 groups Q which can be the same or        different; C₁-C₈-arylalkyloxy that can be substituted by up to 6        groups Q which can be the same or different;        C₁-C₈-arylalkylsulfanyl that can be substituted by up to 6        groups Q which can be the same or different; or        C₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q        which can be the same or different; or    -   two substituent X together with the consecutive carbon atoms to        which they are linked can form a 5- or 6-membered, saturated        carbocycle or saturated heterocycle, which can be substituted by        up to four groups Q which can be the same or different;    -   Z¹ and Z² independently represent a hydrogen atom; a halogen        atom; cyano; substituted or non-substituted C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted or        non-substituted C₁-C₈-alkoxy; substituted or non-substituted        C₁-C₈-alkylsulfanyl; or substituted or non-substituted        C₁-C₈-alkoxycarbonyl; or Z¹ and Z² are a C₂-C₅-alkylene group        that can be substituted by up to four C₁-C₈-alkyl groups;    -   Z³ and Z⁴ independently represent a substituted or        non-substituted C₁-C₈-alkyl;    -   Z⁵ and Z⁶ independently represent a hydrogen atom; a halogen        atom; cyano; substituted or non-substituted C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted or        non-substituted C₁-C₈-alkoxy; substituted or non-substituted        C₁-C₈-alkylsulfanyl; or substituted or non-substituted        C₁-C₈-alkoxycarbonyl; or Z⁵ and Z⁶ are a C₂-C₅-alkylene group        that can be substituted by up to four C₁-C₈-alkyl groups;    -   Z⁷ represents a hydrogen atom; a formyl group; a substituted or        non-substituted C₁-C₈-alkyl; a substituted or non substituted        C₁-C₈-alkoxy; a non-substituted C₃-C₇-cycloalkyl or a        C₃-C₇-cycloalkyl substituted by up to 10 atoms or groups that        can be the same or different and that can be selected in the        list consisting of halogen atoms, cyano, C₁-C₈-alkyl,        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl        comprising up to 9 halogen atoms that can be the same or        different, C₁-C₈-alkylaminocarbonyl and        di-C₁-C₈-alkylaminocarbonyl;    -   Q independently represents a halogen atom; cyano; nitro;        substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        having 1 to 9 halogen atoms that can be the same or different;        substituted or non-substituted C₁-C₈-alkoxy;        C₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms that can be the        same or different; substituted or non-substituted        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 9        halogen atoms that can be the same or different; substituted or        non-substituted tri(C₁-C₈-alkyl)silyl; substituted or        non-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; substituted        or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted        or non-substituted (benzyloxyimino)-C₁-C₈-alkyl;    -   R independently represents hydrogen atom; halogen atom; nitro;        cyano; hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl;        substituted or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;        substituted or non-substituted (benzyloxyimino)-C₁-C₈-alkyl;        substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl        having 1 to 5 halogen atoms; substituted or non-substituted        C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl having 1 to 5 halogen        atoms; substituted or non-substituted C₂-C₈-alkynyl;        C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms; substituted        or non-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having 1        to 5 halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5        halogen atoms; substituted or non-substituted        C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;        substituted or non-substituted di-C₁-C₈-alkylamino; substituted        or non-substituted C₂-C₈-alkenyloxy; substituted or        non-substituted C₃-C₈-alkynyloxy; substituted or non-substituted        C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5 halogen        atoms; substituted or non-substituted tri(C₁-C₈-alkyl)silyl;        substituted or non-substituted C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms;        substituted or non-substituted C₁-C₈-alkylcarbamoyl; substituted        or non-substituted di-C₁-C₈-alkylcarbamoyl; phenoxy;        phenylsulfanyl; phenylamino; benzyloxy; benzylsulfanyl; or        benzylamino;    -   as well as its salts, N-oxides, metal complexes, metallic        complexes and optically active isomers.

For the compounds according to the invention, the following genericterms are generally used with the following meanings:

-   -   halogen means fluorine, bromine, chlorine or iodine.    -   carboxy means —C(═O)OH;    -   carbonyl means —C(═O)—;    -   carbamoyl means —C(═O)NH₂;    -   N-hydroxycarbamoyl means —C(═O)NHOH;    -   SO represents a sulfoxyde group;    -   SO₂ represents a sulfone group;    -   an alkyl group, an alkenyl group and an alkynyl group as well as        moieties containing these terms, can be linear or branched;    -   the aryl moiety contained in an aryl group, an arylalkyl group,        an arylalkenyl group and an arylalkynyl group as well as        moieties containing these terms, can be a phenyl group that can        be substituted by up to 5 groups Q which can be the same or        different, a naphthyl group that can be substituted by up to 7        groups Q which can be the same or different or a pyridyl group        that can be substituted by up to 4 groups Q which can be the        same or different;    -   and, heteroatom means sulfur, nitrogen or oxygen.    -   in the case of an amino group or the amino moiety of any other        amino-comprising group, substituted by two substituent that can        be the same or different, the two substituent together with the        nitrogen atom to which they are linked can form a heterocyclyl        group, preferably a 5- to 7-membered heterocyclyl group, that        can be substituted or that can include other hetero atoms, for        example a morpholino group or piperidinyl group.    -   unless indicated otherwise, a group or a substituent that is        substituted according to the invention can be substituted by one        or more of the following groups or atoms: a halogen atom, a        nitro group, a hydroxy group, a cyano group, an amino group, a        sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a formyl group,        a formyloxy group, a formylamino group, a carbamoyl group, a        N-hydroxycarbamoyl group, a carbamate group, a        (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₁-C₈-cycloalkyl,        tri(C₁-C₈-alkyl)silyl-C₁-C₈-cycloalkyl, a C₁-C₈-halogenoalkyl        having 1 to 5 halogen atoms, a C₁-C₈-halogenocycloalkyl having 1        to 5 halogen atoms, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a        C₂-C₈-alkenyloxy, a C₂-C₈-alkynyloxy, a C₁-C₈-alkylamino, a        di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, a        C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5        halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        N—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, a        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having        1 to 5 halogen atoms, a C₁-C₈-alkylcarbonylamino, a        C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a        C₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, a        C₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulfinyl, a        C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonyl having 1 to 5        halogen atoms, a C₁-C₈-alkylaminosulfamoyl, a        di-C₁-C₈-alkylaminosulfamoyl, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,        a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a 2-oxopyrrolidin-1-yl,        (benzyloxyimino)-C₁-C₆-alkyl, C₁-C₈-alkoxyalkyl,        C₁-C₈-halogenoalkoxyalkyl having 1 to 5 halogen atoms,        benzyloxy, benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl,        or phenylamino.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions)and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the relative position (syn/antior cis/trans) of the substituents of ring B. The invention thus relatesequally to all syn/anti (or cis/trans) isomers and to all possiblesyn/anti (or cis/trans) mixtures, in all proportions. The syn/anti (orcis/trans) isomers can be separated according to general methods, whichare known per se by the man ordinary skilled in the art.

Any of the compounds of formula (I) wherein X represents a hydroxy, asulfanyl group or an amino group may be found in its tautomeric formresulting from the shift of the proton of said hydroxy, sulfanyl oramino group. Such tautomeric forms of such compounds are also part ofthe present invention. More generally speaking, all tautomeric forms ofcompounds of formula (I) wherein X represents a hydroxy, a sulfanylgroup or an amino group, as well as the tautomeric forms of thecompounds which can optionally be used as intermediates in thepreparation processes and which will be defined in the description ofthese processes, are also part of the present invention.

Preferred compounds according to the invention are compounds of formula(I) wherein A is selected in the list consisting of:

-   -   a carbocycle of formula (A¹)

wherein:R¹ represents a halogen atom; a hydroxy group; an amino group; a cyanogroup; substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different;R² to R⁵ that can be the same or different represent a hydrogen atom; ahalogen atom; a hydroxy group; an amino group; a cyano group;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different;

-   -   a heterocycle of formula (A²)

wherein:R⁶ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R⁷ to R⁹ that can be the same or different represent a hydrogen atom; ahalogen atom; a hydroxy group; an amino group; a cyano group;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different;

-   -   a heterocycle of formula (A³)        wherein:        R¹⁰ represents a halogen atom; a hydroxy group; an amino group,        a cyano group; substituted or non-substituted C₁-C₅-alkyl;        C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be        the same or different; substituted or non-substituted        C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5 halogen        atoms that can be the same or different; substituted or        non-substituted C₁-C₅-alkylsulfanyl or        C₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms        that can be the same or different;        R¹¹ to R¹³ that can be the same or different represent a        hydrogen atom; a halogen atom; a hydroxy group; an amino group;        a cyano group; substituted or non-substituted C₁-C₅-alkyl;        C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be        the same or different; substituted or non-substituted        C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5 halogen        atoms that can be the same or different; substituted or        non-substituted C₁-C₅-alkylsulfanyl or        C₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms        that can be the same or different;    -   a heterocycle of formula (A⁴)

wherein:R¹⁴ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R¹⁵ to R¹⁷ that can be the same or different represent a hydrogen atom;a halogen atom; a hydroxy group; an amino group; a cyano group;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different;

-   -   a heterocycle of formula (A⁵)

wherein:R¹⁸ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R¹⁹ and R²⁰ that can be the same or different represent a hydrogen atom;a halogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A⁶)

wherein:R²¹ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R²² and R²³ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁷)

wherein:R²⁴ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R²⁵ and R²⁶ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁶)

wherein:R²⁷ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R²⁸ and R²⁹ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁹)

wherein:R³⁰ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R³¹ and R³² that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹⁰)

wherein:R³³ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different;R³⁴ and R³⁵ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;

More preferred compounds according to the invention are compounds offormula (I) wherein A is selected in the list consisting of A¹; A³; A⁵and A⁶ as herein-defined.

Even more preferred compounds according to the invention are compoundsof formula (I) wherein A represents A¹ wherein R¹ represents a halogenatom, substituted or non-substituted C₁-C₅-alkyl, C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different andR² to R⁵ represent a hydrogen atom.

Other even more preferred compounds according to the invention arecompounds of formula (I) wherein A represents A³ wherein R¹⁰ representsa halogen atom or C₁-C₅-halogenoalkyl comprising up to 5 halogen atomsthat can be the same or different and R¹¹ to R¹³ represent a hydrogenatom.

Other even more preferred compounds according to the invention arecompounds of formula (I) wherein A represents A⁵ wherein R¹⁸ representsa halogen atom or C₁-C₅-halogenoalkyl comprising up to 5 halogen atomsthat can be the same or different and R¹⁹ and R²⁰ represent a hydrogenatom.

Other even more preferred compounds according to the invention arecompounds of formula (I) wherein A represents A⁶ wherein R²¹ representsa non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different and R²² and R²³represent a hydrogen atom.

Other preferred compounds according to the invention are compounds offormula (I) wherein T represents O.

Other preferred compounds according to the invention are compounds offormula (I) wherein B represents a substituted or non-substituted phenylring or a substituted or non-substituted naphthyl ring. Even morepreferably, B represents a substituted or non-substituted phenyl ring.

Other preferred compounds according to the invention are compounds offormula (I) wherein X independently represents a halogen atom;substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;substituted or non-substituted tri(C₁-C₈-alkyl)silyl; substituted ornon-substituted C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different; or wherein twoconsecutive substituents X together with the phenyl ring form asubstituted or non substituted 1,3-benzodioxolyl;1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl;1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z¹, Z², Z⁵ and Z⁶ independently represent a hydrogenatom, a substituted or non-substituted C₁-C₈-alkyl or a substituted ornon-substituted C₁-C₈-alkoxy.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z³ and Z⁴ independently represent a non-substitutedC₁-C₈-alkyl. More preferably, Z³ and Z⁴ independently represent anon-substituted C₁-C₃-alkyl. Even more preferably, Z³ and Z⁴ representmethyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z⁷ represents a hydrogen atom, a non-substitutedC₃-C₇ cycloalkyl or a C₃-C₇ cycloalkyl substituted by up to 10 groups oratoms that can be the same or different and that can be selected in thelist consisting of halogen atoms, C₁-C₈-alkyl, C₁-C₈-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different,C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different. More preferably Z⁷ represents anon-substituted C₃-C₇-cycloalkyl; even more preferably Z⁷ representscyclopropyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein R independently represents a hydrogen atom; halogenatom; cyano; substituted or non-substituted C₁-C₈-alkylamino;substituted or non-substituted di-C₁-C₈-alkylamino; substituted ornon-substituted tri(C₁-C₈-alkyl)silyl; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 5 halogen atoms thatcan be the same or different; substituted or non-substitutedC₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 5 halogen atoms thatcan be the same or different; substituted or non-substitutedC₁-C₈-alkylsulfanyl; amino; hydroxyl; nitro; substituted ornon-substituted C₁-C₈-alkoxycarbonyl; substituted or non-substitutedC₂-C₈-alkynyloxy.

The above mentioned preferences with regard to the substituents of thecompounds according to the invention can be combined in various manners.These combinations of preferred features thus provide sub-classes ofcompounds according to the invention. Examples of such sub-classes ofpreferred compounds according to the invention can be combined:

-   -   preferred features of A with preferred features of B, Z¹, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of B with preferred features of A, Z¹, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of Z¹ with preferred features of A, B, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of Z² with preferred features of A, B, Z¹,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of Z³ with preferred features of A, B, Z¹,        Z², Z⁴, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of Z⁴ with preferred features of A, B, Z¹,        Z², Z³, Z⁵, Z⁶, Z⁷, X, T and R;    -   preferred features of Z⁵ with preferred features of A, B, Z¹,        Z², Z³, Z⁴, Z⁶, Z⁷, X, T and R;    -   preferred features of Z⁶ with preferred features of A, B, Z¹,        Z², Z³, Z⁴, Z⁵, Z⁷, X, T and R;    -   preferred features of Z⁷ with preferred features of A, B, Z¹,        Z², Z³, Z⁴, Z⁵, Z⁶, X, T and R;    -   preferred features of X with preferred features of A, B, Z¹, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, T and R;    -   preferred features of T with preferred features of A, B, Z¹, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, X and R;    -   preferred features of R with preferred features of A, B, Z¹, Z²,        Z³, Z⁴, Z⁵, Z⁶, Z⁷, T and X;

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of A, B, Z¹,Z², Z³, Z⁴, Z⁵, Z⁶, Z⁷, T, X and R, so as to form most preferredsubclasses of compounds according to the invention.

The present invention also relates to a process for the preparation ofthe compound of formula (I).

Thus, according to a further aspect of the present invention there isprovided a process P1 for the preparation of a compound of formula (I)as herein-defined and wherein T represents O and that comprises reactinga N-[(trisubstitutedsilyl)methyl]amine derivative of formula (II) or oneof its salts:

wherein B, n, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶ and Z⁷ are as herein-defined; witha carboxylic acid derivative of formula (III):

wherein A is as herein-defined and L¹ represents a leaving groupselected in the list consisting of a halogen atom, a hydroxyl group,—OR^(a), —OC(═O)R^(a), R^(a) being a substituted or non-substitutedC₁-C₆-alkyl, a substituted or non-substituted C₁-C₆-haloalkyl, a benzyl,4-methoxybenzyl or pentafluorophenyl group, or a group of formulaO—C(═O)A; in the presence of a catalyst and in the presence of acondensing agent in case L¹ represents a hydroxyl group, and in thepresence of an acid binder in case L¹ represents a halogen atom.

N-[(trisubstitutedsilyl)methyl]amine derivatives of formula (II) whereinZ⁷ is a substituted or non-substituted C₁-C₈-alkyl or a substituted ornon-substituted C₃-C₇-cycloalkyl, can be prepared by known processessuch as the nucleophilic substitution of a(halogenomethyl)-(dialkyl)arylsilane by the corresponding primary amine(Journal of Organometallic Chemistry (1978), 153, 193).N-[(trisubstitutedsilyl)methyl]amine derivatives of formula (II) whereinZ⁷ is a hydrogen atom can be prepared by known processes such as thenucleophilic substitution of a (halogenomethyl)(dialkyl)arylsilane byammonia (Journal of the Americam Chemical Society (1951), 73, 3867) orby phthalimide followed a deprotection by hydrazine (patent applicationEP0291787). Furthermore N-[(trisubstitutedsilyl)methyl]amine derivativesof formula (II) wherein Z⁷ is a substituted or non-substitutedC₁-C₈-alkyl or a substituted or non-substituted C₃-C₇-cycloalkyl, can beprepared by known processes from N-[(trisubstitutedsilyl)methyl]aminederivatives of formula (II) wherein Z⁷ is a hydrogen atom by reductiveamination with an aldehyde or ketone, or by nucleophilic substitution ofa halogeno(cyclo)alkyl (Journal of Organic Chemistry (2005), 70, 8372).

Carboxylic acid derivatives of formula (III) can be prepared by knownprocesses.

In case L¹ represents a hydroxy group, the process according to thepresent invention is conducted in the presence of condensing agent.Suitable condensing agent may be selected in the non limited listconsisting of acid halide former, such as phosgene, phosphoroustribromide, phosphorous trichloride, phosphorous pentachloride,phosphorous trichloride oxide or thionyl chloride; anhydride former,such as ethyl chloroformate, methyl chloroformate, isopropylchloroformate, isobutyl chloroformate or methanesulfonyl chloride;carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC) or othercustomary condensing agents, such as phosphorous pentoxide,polyphosphoric acid, N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloro-methane,4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloridehydrate, bromo-tripyrrolidino-phosphonium-hexafluorophosphate orpropanephosphonic anhydride (T3P).

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be selected in the listconsisting of 4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole ordimethylformamide.

In case L¹ represents a halogen atom, the process according to thepresent invention is conducted in the presence of an acid binder.Suitable acid binders for carrying out process P1 according to theinvention are in each case all inorganic and organic bases that arecustomary for such reactions. Preference is given to using alkalineearth metal, alkali metal hydride, alkali metal hydroxides or alkalimetal alkoxides, such as sodium hydroxide, sodium hydride, calciumhydroxide, potassium hydroxide, potassium tert-butoxide or otherammonium hydroxide, alkali metal carbonates, such as cesium carbonate,sodium carbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate, alkali metal or alkaline earth metal acetates, such assodium acetate, potassium acetate, calcium acetate and also tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclo-nonene (DBN) or diazabicycloundecene (DBU).

It is also possible to work in the absence of an additional condensingagent or to employ an excess of the amine component, so that itsimultaneously acts as acid binder agent.

According to a further aspect according to the invention, there isprovided a process P2 for the preparation of a compound of formula (I)wherein T represents S, starting from a compound of formula (I) whereinT represents O and illustrated according to the following reactionscheme:

wherein A, B, n, Z¹, Z², Z³, Z⁴, Z⁵, Z⁶ and Z⁷ are as herein-defined, inthe optional presence of a catalytic or stoechiometric or more, quantityof a base such as an inorganic and organic base. Preference is given tousing alkali metal carbonates, such as sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate; heterocyclicaromatic bases, such as pyridine, picoline, lutidine, collidine; andalso tertiary amines, such as trimethylamine, triethylamine,tributylamine, N,N-dimethylaniline, N,N-dimethylaminopyridine orN-methyl-piperidine.

Process P2 according to the invention is performed in the presence of athionating agent.

Starting amide derivatives of formula (I) can be prepared according toprocesses P1.

Suitable thionating agents for carrying out process P2 according to theinvention can be sulfur (S), sulfhydric acid (H₂S), sodium sulfide(Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃),bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S),phosphorous pentasulfide (P₂S₅), Lawesson's reagent(2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) ora polymer-supported thionating reagent such as described in Journal ofthe Chemical Society, Perkin 1 (2001), 358.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesize.

Still in a further aspect, the present invention relates to compounds offormula (II) useful as intermediate compounds or materials for theprocess of preparation according to the invention. The present inventionthus provides compounds of formula (IIa):

wherein B, n, Z¹, Z², Z⁵ and Z⁶ are as herein-defined with the exclusionof:

-   1-[dimethyl(phenyl)silyl]methanamine and its hydrochloride salt-   1-[dimethyl(phenyl)silyl]ethanamine and its hydrochloride salt-   (1R)-1-[dimethyl(phenyl)silyl]ethanamine-   1-[dimethyl(phenyl)silyl]propan-1-amine-   1-[dimethyl(phenyl)silyl]pentan-1-amine and its hydrochloride salt-   1-[dimethyl(phenyl)silyl]octan-1-amine-   1-[(4-methoxyphenyl)(dimethyl)silyl]methanamine-   1-[(3-fluorophenyl)(dimethyl)silyl]methanamine and its hydrochloride    salt-   1-[(4-fluorophenyl)(dimethyl)silyl]methanamine-   1-[(4-chlorophenyl)(dimethyl)silyl]methanamine-   1-[benzyl(dimethyl)silyl]methanamine and its hydrochloride salt-   1-[(2-fluorobenzyl)(dimethyl)silyl]methanamine and its hydrochloride    salt-   1-[(3-fluorobenzyl)(dimethyl)silyl]methanamine and its hydrochloride    salt-   1-[(4-fluorobenzyl)(dimethyl)silyl]methanamine and its hydrochloride    salt-   1-[(4-chlorobenzyl)(dimethyl)silyl]methanamine-   1-[(2,4-difluorobenzyl)(dimethyl)silyl]methanamine and its    hydrochloride salt-   1-[(2,6-difluorobenzyl)(dimethyl)silyl]methanamine and its    hydrochloride salt-   1-[(3,4-difluorobenzyl)(dimethyl)silyl]methanamine and its    hydrochloride salt-   1-[(3,5-difluorobenzyl)(dimethyl)silyl]methanamine-   1-[(3,4-dichlorobenzyl)(dimethyl)silyl]methanamine-   1-[dimethyl(2-thienylmethyl)silyl]methanamine.

The present invention thus also provides compounds of formula (IIb):

wherein B, n, Z¹, Z², Z⁵ and Z⁶ are as herein-defined, and Z⁷ representsa cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl groupwith the exclusion of:

-   N-{[dimethyl-(phenyl)silyl]methyl}cyclohexanamine.

On the basis of the present description and his general knowledge and ofavailable publications as for example Journal of OrganometallicChemistry (1978), 153, 193 or Journal of Organic Chemistry (2005), 70,8372, the skilled person can prepare intermediate compound of formula(II) according to the present invention.

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention that is sufficient to control ordestroy the fungi present or liable to appear on the crops and that doesnot entail any appreciable symptom of phytotoxicity for the said crops.Such an amount can vary within a wide range depending on the fungus tobe controlled, the type of crop, the climatic conditions and thecompounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials thatare within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with that the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports can also beused.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulfonic acid salts, phenolsulfonic or naphthalenesulfonicacid salts, polycondensates of ethylene oxide with fatty alcohols orwith fatty acids or with fatty amines, substituted phenols (inparticular alkylphenols or arylphenols), salts of sulfosuccinic acidesters, taurine derivatives (in particular alkyl taurates), phosphoricesters of polyoxyethylated alcohols or phenols, fatty acid esters ofpolyols and derivatives of the above compounds containing sulfate,sulfonate and phosphate functions. The presence of at least onesurfactant is generally essential when the active compound and/or theinert support are water-insoluble and when the vector agent for theapplication is water. Preferably, surfactant content can be comprisedfrom 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, that complies withthe usual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions that are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions that must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.

The compounds of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops.

Thus, according to a further aspect of the invention, there is provideda method for curatively or preventively controlling the phytopathogenicfungi of plants or crops characterised in that a compound of formula (I)or a fungicide composition according to the invention is applied to theseed, the plant or to the fruit of the plant or to the soil wherein theplant is growing or wherein it is desired to grow.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

According to the invention all plants and plant parts can be treated. Byplants is meant all plants and plant populations such as desirable andundesirable wild plants, cultivars and plant varieties (whether or notprotectable by plant variety or plant breeder's rights). Cultivars andplant varieties can be plants obtained by conventional propagation andbreeding methods which can be assisted or supplemented by one or morebiotechnological methods such as by use of double haploids, protoplastfusion, random and directed mutagenesis, molecular or genetic markers orby bioengineering and genetic engineering methods. By plant parts ismeant all above ground and below ground parts and organs of plants suchas shoot, leaf, blossom and root, whereby for example leaves, needles,stems, branches, blossoms, fruiting bodies, fruits and seed as well asroots, corms and rhizomes are listed. Crops and vegetative andgenerative propagating material, for example cuttings, corms, rhizomes,runners and seeds also belong to plant parts.

Among the plants that can be protected by the method according to theinvention, mention may be made of major field crops like corn, soybean,cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassicarapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat,sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vineand various fruits and vegetables of various botanical taxa such asRosaceae sp. (for instance pip fruit such as apples and pears, but alsostone fruit such as apricots, cherries, almonds and peaches, berryfruits such as strawberries), Ribesioidae sp., Juglandaceae sp.,Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceaesp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance bananatrees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges andgrapefruit); Solanaceae sp. (for instance tomatoes, potatoes, peppers,eggplant), Liliaceae sp., Compositiae sp. (for instance lettuce,artichoke and chicory—including root chicory, endive or common chicory),Umbelliferae sp. (for instance carrot, parsley, celery and celeriac),Cucurbitaceae sp. (for instance cucumber—including pickling cucumber,squash, watermelon, gourds and melons), Alliaceae sp. (for instanceonions and leek), Cruciferae sp. (for instance white cabbage, redcabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi,radish, horseradish, cress, Chinese cabbage), Leguminosae sp. (forinstance peanuts, peas and beans beans—such as climbing beans and broadbeans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach,beetroots), Malvaceae (for instance okra), Asparagaceae (for instanceasparagus); horticultural and forest crops; ornamental plants; as wellas genetically modified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants ofwhich a heterologous gene has been stably integrated into genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, cosuppression technology, RNAinterference—RNAi—technology or microRNA—miRNA—technology). Aheterologous gene that is located in the genome is also called atransgene. A transgene that is defined by its particular location in theplant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf color, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted microorganisms. This may, ifappropriate, be one of the reasons of the enhanced activity of thecombinations according to the invention, for example against fungi.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances orcombinations of substances which are capable of stimulating the defensesystem of plants in such a way that, when subsequently inoculated withunwanted microorganisms, the treated plants display a substantial degreeof resistance to these microorganisms. In the present case, unwantedmicroorganisms are to be understood as meaning phytopathogenic fungi,bacteria and viruses. Thus, the substances according to the inventioncan be employed for protecting plants against attack by theabovementioned pathogens within a certain period of time after thetreatment. The period of time within which protection is effectedgenerally extends from 1 to 10 days, preferably 1 to 7 days, after thetreatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids. Examples ofnematode resistant plants are described in e.g. U.S. patent applicationSer. Nos. 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479,10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253,12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947,12/252,453, 12/209,354, 12/491,396, 12/497,221, 12/644,632, 12/646,004,12/701,058, 12/718,059, 12/721,595, 12/638,591 and in WO11/002992,WO11/014749, WO11/103247, WO11/103248.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stresses). Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male sterile plants and sold to growers.Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 92/05251, WO 95/09910, WO 98/27806, WO05/002324, WO 06/021972 and U.S. Pat. No. 6,229,072). However, geneticdeterminants for male sterility can also be located in the nucleargenome. Male sterile plants can also be obtained by plant biotechnologymethods such as genetic engineering. A particularly useful means ofobtaining male-sterile plants is described in WO 89/10396 in which, forexample, a ribonuclease such as barnase is selectively expressed in thetapetum cells in the stamens. Fertility can then be restored byexpression in the tapetum cells of a ribonuclease inhibitor such asbarstar (e.g. WO 91/02069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-resistant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., 1983,Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genesencoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), aTomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or anEleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS asdescribed in for example EP 0837944, WO 00/66746, WO 00/66747,WO02/26995, WO11/000498. Glyphosate-tolerant plants can also be obtainedby expressing a gene that encodes a glyphosate oxido-reductase enzyme asdescribed in U.S. Pat. Nos. 5,776,760 and 5,463,175. Glyphosate-tolerantplants can also be obtained by expressing a gene that encodes aglyphosate acetyl transferase enzyme as described in for example WO02/36782, WO 03/092360, WO 05/012515 and WO 07/024782.Glyphosate-tolerant plants can also be obtained by selecting plantscontaining naturally-occurring mutations of the above-mentioned genes,as described in for example WO 01/024615 or WO 03/013226. Plantsexpressing EPSPS genes that confer glyphosate tolerance are described ine.g. U.S. patent application Ser. Nos. 11/517,991, 10/739,610,12/139,408, 12/352,532, 11/312,866, 11/315,678, 12/421,292, 11/400,598,11/651,752, 11/681,285, 11/605,824, 12/468,205, 11/760,570, 11/762,526,11/769,327, 11/769,255, 11/943801 or 12/362,774. Plants comprising othergenes that confer glyphosate tolerance, such as decarboxylase genes, aredescribed in e.g. U.S. patent application Ser. Nos. 11/588,811,11/185,342, 12/364,724, 11/185,560 or 12/423,926.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition, e.g. described in U.S.patent application Ser. No. 11/760,602. One such efficient detoxifyingenzyme is an enzyme encoding a phosphinothricin acetyltransferase (suchas the bar or pat protein from Streptomyces species). Plants expressingan exogenous phosphinothricin acetyltransferase are for exampledescribed in U.S. Pat. Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894;5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). HPPD is an enzyme that catalyze the reaction in whichpara-hydroxyphenylpyruvate (HPP) is transformed into homogentisate.Plants tolerant to HPPD-inhibitors can be transformed with a geneencoding a naturally-occurring resistant HPPD enzyme, or a gene encodinga mutated or chimeric HPPD enzyme as described in WO 96/38567, WO99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, or U.S. Pat. No.6,768,044, WO11/076877, WO11/076882, WO11/076885, WO11/076889,WO11/076892. Tolerance to HPPD-inhibitors can also be obtained bytransforming plants with genes encoding certain enzymes enabling theformation of homogentisate despite the inhibition of the native HPPDenzyme by the HPPD-inhibitor. Such plants and genes are described in WO99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors canalso be improved by transforming plants with a gene encoding an enzymehaving prephenate deshydrogenase (PDH) activity in addition to a geneencoding an HPPD-tolerant enzyme, as described in WO 2004/024928.Further, plants can be made more tolerant to HPPD-inhibitor herbicidesby adding into their genome a gene encoding an enzyme capable ofmetabolizing or degrading HPPD inhibitors, such as the CYP450 enzymesshown in WO 2007/103567 and WO 2008/150473.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright (2002, Weed Science 50:700-712), but also, in U.S.Pat. Nos. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The productionof sulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361;5,731,180; 5,304,732; 4,761,373; 5,331,107; 5,928,937; and 5,378,824;and international publication WO 96/33270. Other imidazolinone-tolerantplants are also described in for example WO 2004/040012, WO 2004/106529,WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO2006/024351, and WO 2006/060634. Further sulfonylurea- andimidazolinone-tolerant plants are also described in for example WO07/024782, WO11/076345, WO2012058223 and US Patent Application No61/288958.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 97/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 01/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al. (1998, Microbiology        and Molecular Biology Reviews, 62: 807-813), updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:        http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or        insecticidal portions thereof, e.g., proteins of the Cry protein        classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F, Cry2Ab,        Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP        1999141 and WO 2007/107302), or such proteins encoded by        synthetic genes as e.g. described in and U.S. patent application        Ser. No. 12/249,016; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19:        668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71,        1765-1774) or the binary toxin made up of the Cry1A or Cry1F        proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A. 105 protein produced by        corn event MON89034 (WO 2007/027777); or    -   4) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation, such as the        Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A        protein in corn event MIR604; or    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:        http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        94/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 5) to 7) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102; or    -   9) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a crystal        protein from Bacillus thuringiensis, such as the binary toxin        made up of VIP3 and Cry1A or Cry1F (US Patent Appl. No.        61/126,083 and 61/195,019), or the binary toxin made up of the        VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5).    -   10) a protein of 9) above wherein some, particularly 1 to 10,        amino acids have been replaced by another amino acid to obtain a        higher insecticidal activity to a target insect species, and/or        to expand the range of target insect species affected, and/or        because of changes introduced into the encoding DNA during        cloning or transformation (while still encoding an insecticidal        protein)

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 10. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 10, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

An “insect-resistant transgenic plant”, as used herein, further includesany plant containing at least one transgene comprising a sequenceproducing upon expression a double-stranded RNA which upon ingestion bya plant insect pest inhibits the growth of this insect pest, asdescribed e.g. in WO 2007/080126, WO 2006/129204, WO 2007/074405, WO2007/080127 and WO 2007/035650.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   1) plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose) polymerase        (PARP) gene in the plant cells or plants as described in WO        00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5.    -   2) plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   3) plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotineamide        adenine dinucleotide salvage synthesis pathway including        nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic        acid mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphorybosyltransferase as described e.g. in EP 04077624.7, WO        2006/133827, PCT/EP07/002433, EP 1999263, or WO 2007/107326.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO 95/04826,        EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188,        WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545,        WO 98/27212, WO 98/40503, WO99/58688, WO 99/58690, WO 99/58654,        WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229,        WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO        2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO        2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO        2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO        00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP        06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP        07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO        2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145,        WO 99/12950, WO 99/66050, WO 99/53072, U.S. Pat. No. 6,734,341,        WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509,        WO 2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No.        6,013,861, WO 94/04693, WO 94/09144, WO 94/11520, WO 95/35026,        WO 97/20936, WO 10/012796, WO 10/003701    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460,        and WO 99/24593, plants producing alpha-1,4-glucans as disclosed        in WO 95/31553, US 2002031826, U.S. Pat. No. 6,284,479, U.S.        Pat. No. 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO        00/14249, plants producing alpha-1,6 branched alpha-1,4-glucans,        as disclosed in WO 00/73422, plants producing alternan, as        disclosed in e.g. WO 00/47727, WO 00/73422, EP 06077301.7, U.S.        Pat. No. 5,908,975 and EP 0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006304779, and WO 2005/012529.    -   4) transgenic plants or hybrid plants, such as onions with        characteristics such as ‘high soluble solids content’, ‘low        pungency’ (LP) and/or ‘long storage’ (LS), as described in U.S.        patent application Ser. No. 12/020,360 and 61/054,026.    -   5) Transgenic plants displaying an increase yield as for example        disclosed in WO11/095528

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 98/00549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in WO        2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 01/17333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO 02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiber-selective β-1,3-glucanase        as described in WO 2005/017157, or as described in EP 08075514.3        or US Patent Appl. No. 61/128,938    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acetylglucosaminetransferase gene including nodC and chitin        synthase genes as described in WO 2006/136351 WO11/089021,        WO2012074868

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered oil profile characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. No.        5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or        U.S. Pat. No. 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. No.        6,270,828, U.S. Pat. No. 6,169,190, U.S. Pat. No. 5,965,755, or        WO11/060946.    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283 or U.S. patent application Ser. No. 12/668,303    -   d) Plants such as oilseed rape plants, producing oil having an        aleter glucosinolate content as described in WO2012075426.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered seed shattering characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered seed shattering characteristics andinclude plants such as oilseed rape plants with delayed or reduced seedshattering as described in U.S. Patent Appl. No. 61/135,230,WO09/068313, WO10/006732 and WO2012090499.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as Tobacco plants, with alteredpost-translational protein modification patterns, for example asdescribed in WO 10/121818 and WO 10/145846

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are the subject of petitionsfor non-regulated status, in the United States of America, to the Animaland Plant Health Inspection Service (APHIS) of the United StatesDepartment of Agriculture (USDA) whether such petitions are granted orare still pending. At any time this information is readily availablefrom APHIS (4700 River Road Riverdale, Md. 20737, USA), for instance onits internet site (URL http://www.aphis.usda.gov/brs/not_reg.html). Onthe filing date of this application the petitions for nonregulatedstatus that were pending with APHIS or granted by APHIS were those whichcontains the following information:

-   -   Petition: the identification number of the petition. Technical        descriptions of the transformation events can be found in the        individual petition documents which are obtainable from APHIS,        for example on the APHIS website, by reference to this petition        number. These descriptions are herein incorporated by reference.    -   Extension of Petition: reference to a previous petition for        which an extension is requested.    -   Institution: the name of the entity submitting the petition.    -   Regulated article: the plant species concerned.    -   Transgenic phenotype: the trait conferred to the plants by the        transformation event.    -   Transformation event or line: the name of the event or events        (sometimes also designated as lines or lines) for which        nonregulated status is requested.    -   APHIS documents: various documents published by APHIS in        relation to the Petition and which can be requested with APHIS.

Additional particularly useful plants containing single transformationevents or combinations of transformation events are listed for examplein the databases from various national or regional regulatory agencies(see for example http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agenciesincluding Event 1143-14A (cotton, insect control, not deposited,described in WO2006/128569); Event 1143-51B (cotton, insect control, notdeposited, described in WO2006/128570); Event 1445 (cotton, herbicidetolerance, not deposited, described in US2002120964 or WO2002/034946);Event 17053 (rice, herbicide tolerance, deposited as PTA-9843, describedin WO2010/117737); Event 17314 (rice, herbicide tolerance, deposited asPTA-9844, described in WO2010/117735); Event 281-24-236 (cotton, insectcontrol—herbicide tolerance, deposited as PTA-6233, described inWO2005/103266 or US2005216969); Event 3006-210-23 (cotton, insectcontrol—herbicide tolerance, deposited as PTA-6233, described inUS2007143876 or WO2005/103266); Event 3272 (corn, quality trait,deposited as PTA-9972, described in WO2006098952 or US2006230473); Event40416 (corn, insect control—herbicide tolerance, deposited as ATCCPTA-11508, described in WO2011/075593); Event 43A47 (corn, insectcontrol—herbicide tolerance, deposited as ATCC PTA-11509, described inWO2011/075595); Event 5307 (corn, insect control, deposited as ATCCPTA-9561, described in WO2010/077816); Event ASR-368 (bent grass,herbicide tolerance, deposited as ATCC PTA-4816, described inUS2006162007 or WO2004053062); Event B16 (corn, herbicide tolerance, notdeposited, described in US2003126634); Event BPS-CV127-9 (soybean,herbicide tolerance, deposited as NCIMB No. 41603, described inWO2010/080829); Event CE43-67B (cotton, insect control, deposited as DSMACC2724, described in US2009217423 or WO2006/128573); Event CE44-69D(cotton, insect control, not deposited, described in US20100024077);Event CE44-69D (cotton, insect control, not deposited, described inWO2006/128571); Event CE46-02A (cotton, insect control, not deposited,described in WO2006/128572); Event COT102 (cotton, insect control, notdeposited, described in US2006130175 or WO2004039986); Event COT202(cotton, insect control, not deposited, described in US2007067868 orWO2005054479); Event COT203 (cotton, insect control, not deposited,described in WO2005/054480); Event DAS40278 (corn, herbicide tolerance,deposited as ATCC PTA-10244, described in WO2011/022469); EventDAS-59122-7 (corn, insect control—herbicide tolerance, deposited as ATCCPTA 11384, described in US2006070139); Event DAS-59132 (corn, insectcontrol—herbicide tolerance, not deposited, described in WO2009/100188);Event DAS68416 (soybean, herbicide tolerance, deposited as ATCCPTA-10442, described in WO2011/066384 or WO2011/066360); EventDP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296,described in US2009137395 or WO2008/112019); Event DP-305423-1 (soybean,quality trait, not deposited, described in US2008312082 orWO2008/054747); Event DP-32138-1 (corn, hybridization system, depositedas ATCC PTA-9158, described in US20090210970 or WO2009/103049); EventDP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287,described in US20100184079 or WO2008/002872); Event EE-1 (brinjal,insect control, not deposited, described in WO2007/091277); Event FI117(corn, herbicide tolerance, deposited as ATCC 209031, described inUS2006059581 or WO1998/044140); Event GA21 (corn, herbicide tolerance,deposited as ATCC 209033, described in US2005086719 or WO1998/044140);Event GG25 (corn, herbicide tolerance, deposited as ATCC 209032,described in US2005188434 or WO1998/044140); Event GHB119 (cotton,insect control—herbicide tolerance, deposited as ATCC PTA-8398,described in WO2008/151780); Event GHB614 (cotton, herbicide tolerance,deposited as ATCC PTA-6878, described in US2010050282 or WO2007/017186);Event GJ11 (corn, herbicide tolerance, deposited as ATCC 209030,described in US2005188434 or WO1998/044140); Event GM RZ13 (sugar beet,virus resistance, deposited as NCIMB-41601, described in WO2010/076212);Event H7-1 (sugar beet, herbicide tolerance, deposited as NCIMB 41158 orNCIMB 41159, described in US2004172669 or WO2004/074492); Event JOPLIN1(wheat, disease tolerance, not deposited, described in US2008064032);Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658,described in WO2006/108674 or US2008320616); Event LL55 (soybean,herbicide tolerance, deposited as NCIMB 41660, described inWO2006/108675 or US2008196127); Event LLcotton25 (cotton, herbicidetolerance, deposited as ATCC PTA-3343, described in WO2003013224 orUS2003097687); Event LLRICE06 (rice, herbicide tolerance, deposited asATCC-23352, described in U.S. Pat. No. 6,468,747 or WO2000/026345);Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600,described in US20082289060 or WO2000/026356); Event LY038 (corn, qualitytrait, deposited as ATCC PTA-5623, described in US2007028322 orWO2005061720); Event MIR162 (corn, insect control, deposited asPTA-8166, described in US2009300784 or WO2007/142840); Event MIR604(corn, insect control, not deposited, described in US2008167456 orWO2005103301); Event MON15985 (cotton, insect control, deposited as ATCCPTA-2516, described in US2004-250317 or WO2002/100163); Event MON810(corn, insect control, not deposited, described in US2002102582); EventMON863 (corn, insect control, deposited as ATCC PTA-2605, described inWO2004/011601 or US2006095986); Event MON87427 (corn, pollinationcontrol, deposited as ATCC PTA-7899, described in WO2011/062904); EventMON87460 (corn, stress tolerance, deposited as ATCC PTA-8910, describedin WO2009/111263 or US20110138504); Event MON87701 (soybean, insectcontrol, deposited as ATCC PTA-8194, described in US2009130071 orWO2009/064652); Event MON87705 (soybean, quality trait—herbicidetolerance, deposited as ATCC PTA-9241, described in US20100080887 orWO2010/037016); Event MON87708 (soybean, herbicide tolerance, depositedas ATCC PTA9670, described in WO2011/034704); Event MON87754 (soybean,quality trait, deposited as ATCC PTA-9385, described in WO2010/024976);Event MON87769 (soybean, quality trait, deposited as ATCC PTA-8911,described in US20110067141 or WO2009/102873); Event MON88017 (corn,insect control—herbicide tolerance, deposited as ATCC PTA-5582,described in US2008028482 or WO2005/059103); Event MON88913 (cotton,herbicide tolerance, deposited as ATCC PTA-4854, described inWO2004/072235 or US2006059590); Event MON89034 (corn, insect control,deposited as ATCC PTA-7455, described in WO2007/140256 or US2008260932);Event MON89788 (soybean, herbicide tolerance, deposited as ATCCPTA-6708, described in US2006282915 or WO2006/130436); Event MS11(oilseed rape, pollination control—herbicide tolerance, deposited asATCC PTA-850 or PTA-2485, described in WO2001/031042); Event MS8,(oilseed rape, pollination control—herbicide tolerance, deposited asATCC PTA-730, described in WO2001/041558 or US2003188347); Event NK603(corn, herbicide tolerance, deposited as ATCC PTA-2478, described inUS2007-292854); Event PE-7 (rice, insect control, not deposited,described in WO2008/114282); Event RF3, (oilseed rape, pollinationcontrol—herbicide tolerance, deposited as ATCC PTA-730, described inWO2001/041558 or US2003188347); Event RT73 (oilseed rape, herbicidetolerance, not deposited, described in WO2002/036831 or US2008070260);Event T227-1 (sugar beet, herbicide tolerance, not deposited, describedin WO2002/44407 or US2009265817); Event T25 (corn, herbicide tolerance,not deposited, described in US2001029014 or WO2001/051654); EventT304-40 (cotton, insect control—herbicide tolerance, deposited as ATCCPTA-8171, described in US2010077501 or WO2008/122406); Event T342-142(cotton, insect control, not deposited, described in WO2006/128568);Event TC1507 (corn, insect control—herbicide tolerance, not deposited,described in US2005039226 or WO2004/099447); Event VIP1034 (corn, insectcontrol—herbicide tolerance, deposited as ATCC PTA-3925., described inWO2003/052073), Event 32316 (corn, insect control-herbicide tolerance,deposited as PTA-11507, described in WO2011/153186A1), Event 4114 (corn,insect control-herbicide tolerance, deposited as PTA-11506, described inWO2011/084621), event EE-GM3/FG72 (soybean, herbicide tolerance, ATCCAccession No PTA-11041, WO2011/063413A2), event DAS-68416-4 (soybean,herbicide tolerance, ATCC Accession No PTA-10442, WO2011/066360A1),event DAS-68416-4 (soybean, herbicide tolerance, ATCC Accession NoPTA-10442, WO2011/066384A1), event DP-040416-8 (corn, insect control,ATCC Accession No PTA-11508, WO2011/075593A1), event DP-043A47-3 (corn,insect control, ATCC Accession No PTA-11509, WO2011/075595A1), eventDP-004114-3 (corn, insect control, ATCC Accession No PTA-11506,WO2011/084621A1), event DP-032316-8 (corn, insect control, ATCCAccession No PTA-11507, WO2011/084632A1), event MON-88302-9 (oilseedrape, herbicide tolerance, ATCC Accession No PTA-10955,WO2011/153186A1), event DAS-21606-3 (soybean, herbicide tolerance, ATCCAccession No. PTA-11028, WO2012/033794A2), event MON-87712-4 (soybean,quality trait, ATCC Accession No. PTA-10296, WO2012/051199A2), eventDAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Accession No.PTA-11336, WO2012/075426A1), event DAS-14536-7 (soybean, stackedherbicide tolerance, ATCC Accession No. PTA-11335, WO2012/075429A1),event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Accession No.PTA-11226, WO2012/082548A2), event DP-061061-7 (oilseed rape, herbicidetolerance, no deposit No available, WO2012071039A1), event DP-073496-4(oilseed rape, herbicide tolerance, no deposit No available,US2012131692), event 8264.44.06.1 (soybean, stacked herbicide tolerance,Accession No PTA-11336, WO2012075426A2), event 8291.45.36.2 (soybean,stacked herbicide tolerance, Accession No. PTA-11335, WO2012075429A2).

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

Powdery mildew diseases such as:

-   -   Blumeria diseases, caused for example by Blumeria graminis;    -   Podosphaera diseases, caused for example by Podosphaera        leucotricha;    -   Sphaerotheca diseases, caused for example by Sphaerotheca        fuliginea;    -   Uncinula diseases, caused for example by Uncinula necator;

Rust diseases such as:

-   -   Gymnosporangium diseases, caused for example by Gymnosporangium        sabinae;    -   Hemileia diseases, caused for example by Hemileia vastatrix;    -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi        or Phakopsora meibomiae;    -   Puccinia diseases, caused for example by Puccinia recondite,        Puccinia graminis or Puccinia striiformis;    -   Uromyces diseases, caused for example by Uromyces        appendiculatus;

Oomycete diseases such as:

-   -   Albugo diseases caused for example by Albugo candida;    -   Bremia diseases, caused for example by Bremia lactucae;    -   Peronospora diseases, caused for example by Peronospora pisi        or P. brassicae;    -   Phytophthora diseases, caused for example by Phytophthora        infestans;    -   Plasmopara diseases, caused for example by Plasmopara viticola;    -   Pseudoperonospora diseases, caused for example by        Pseudoperonospora humuli or Pseudoperonospora cubensis;    -   Pythium diseases, caused for example by Pythium ultimum;

Leafspot, leaf blotch and leaf blight diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria solani;    -   Cercospora diseases, caused for example by Cercospora beticola;    -   Cladiosporum diseases, caused for example by Cladiosporium        cucumerinum;    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus (Conidiaform: Drechslera, Syn: Helminthosporium) or        Cochliobolus miyabeanus;    -   Colletotrichum diseases, caused for example by Colletotrichum        lindemuthanium;    -   Cycloconium diseases, caused for example by Cycloconium        oleaginum;    -   Diaporthe diseases, caused for example by Diaporthe citri;    -   Elsinoe diseases, caused for example by Elsinoe fawcettii;    -   Gloeosporium diseases, caused for example by Gloeosporium        laeticolor;    -   Glomerella diseases, caused for example by Glomerella cingulata;    -   Guignardia diseases, caused for example by Guignardia bidwelli;

Leptosphaeria diseases, caused for example by Leptosphaeria maculans;Leptosphaeria nodorum;

-   -   Magnaporthe diseases, caused for example by Magnaporthe grisea;    -   Mycosphaerella diseases, caused for example by Mycosphaerella        graminicola; Mycosphaerella arachidicola; Mycosphaerella        fijiensis;    -   Phaeosphaeria diseases, caused for example by Phaeosphaeria        nodorum;

Pyrenophora diseases, caused for example by Pyrenophora teres, orPyrenophora tritici repentis;

-   -   Ramularia diseases, caused for example by Ramularia collo-cygni,        or Ramularia areola;    -   Rhynchosporium diseases, caused for example by Rhynchosporium        secalis;    -   Septoria diseases, caused for example by Septoria apii or        Septoria lycopercisi;    -   Typhula diseases, caused for example by Typhula incamata;    -   Venturia diseases, caused for example by Venturia inaequalis;

Root, Sheath and stem diseases such as:

-   -   Corticium diseases, caused for example by Corticium graminearum;    -   Fusarium diseases, caused for example by Fusarium oxysporum;    -   Gaeumannomyces diseases, caused for example by Gaeumannomyces        graminis;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Sarocladium diseases caused for example by Sarocladium oryzae;    -   Sclerotium diseases caused for example by Sclerotium oryzae;    -   Tapesia diseases, caused for example by Tapesia acuformis;    -   Thielaviopsis diseases, caused for example by Thielaviopsis        basicola;

Ear and panicle diseases such as:

-   -   Alternaria diseases, caused for example by Alternaria spp.;    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Cladosporium diseases, caused for example by Cladosporium spp.;    -   Claviceps diseases, caused for example by Claviceps purpurea;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Monographella diseases, caused for example by Monographella        nivalis;

Smut and bunt diseases such as:

-   -   Sphacelotheca diseases, caused for example by Sphacelotheca        reiliana;    -   Tilletia diseases, caused for example by Tilletia caries;    -   Urocystis diseases, caused for example by Urocystis occulta;    -   Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

-   -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Penicillium diseases, caused for example by Penicillium        expansum;    -   Rhizopus diseases caused by example by Rhizopus stolonifer    -   Sclerotinia diseases, caused for example by Sclerotinia        sclerotiorum;    -   Verticilium diseases, caused for example by Verticilium        alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

-   -   Alternaria diseases, caused for example by Alternaria        brassicicola    -   Aphanomyces diseases, caused for example by Aphanomyces        euteiches    -   Ascochyta diseases, caused for example by Ascochyta lentis    -   Aspergillus diseases, caused for example by Aspergillus flavus    -   Cladosporium diseases, caused for example by Cladosporium        herbarum    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus (Conidiaform: Drechslera, Bipolaris Syn:        Helminthosporium);    -   Colletotrichum diseases, caused for example by Colletotrichum        coccodes;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Macrophomina diseases, caused for example by Macrophomina        phaseolina    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Penicillium diseases, caused for example by Penicillium expansum    -   Phoma diseases, caused for example by Phoma lingam    -   Phomopsis diseases, caused for example by Phomopsis sojae;    -   Phytophthora diseases, caused for example by Phytophthora        cactorum;    -   Pyrenophora diseases, caused for example by Pyrenophora graminea    -   Pyricularia diseases, caused for example by Pyricularia oryzae;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Rhizopus diseases, caused for example by Rhizopus oryzae    -   Sclerotium diseases, caused for example by Sclerotium roffsii;    -   Septoria diseases, caused for example by Septoria nodorum;    -   Typhula diseases, caused for example by Typhula incarnata;    -   Verticillium diseases, caused for example by Verticillium        dahliae;

Canker, broom and dieback diseases such as:

-   -   Nectria diseases, caused for example by Nectria gafiigena;

Blight diseases such as:

-   -   Monilinia diseases, caused for example by Monilinia laxa;

Leaf blister or leaf curl diseases such as:

-   -   Exobasidium diseases caused for example by Exobasidium vexans    -   Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

-   -   Esca diseases, caused for example by Phaemoniella clamydospora;    -   Eutypa dyeback, caused for example by Eutypa lata;    -   Ganoderma diseases caused for example by Ganoderma boninense;    -   Rigidoporus diseases caused for example by Rigidoporus lignosus

Diseases of Flowers and Seeds such as

-   -   Botrytis diseases caused for example by Botrytis cinerea;

Diseases of Tubers such as

-   -   Rhizoctonia diseases caused for example by Rhizoctonia solani;    -   Helminthosporium diseases caused for example by Helminthosporium        solani;

Club root diseases such as

-   -   Plasmodiophora diseases, cause for example by Plamodiophora        brassicae.

Diseases caused by Bacterial Organisms such as

-   -   Xanthomonas species for example Xanthomonas campestris pv.        oryzae;    -   Pseudomonas species for example Pseudomonas syringae pv.        lachrymans;    -   Erwinia species for example Erwinia amylovora.

The composition according to the invention may also be used againstfungal diseases liable to grow on or inside timber. The term “timber”means all types of species of wood, and all types of working of thiswood intended for construction, for example solid wood, high-densitywood, laminated wood, and plywood. The method for treating timberaccording to the invention mainly consists in contacting one or morecompounds according to the invention or a composition according to theinvention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The compounds or mixtures according to the invention can also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table of compound examples and the followingpreparation or efficacy examples.

Table 1 illustrates in a non-limiting manner examples of compounds offormula (I) according to the invention:

wherein A can be selected in the list consisting of the followinggroups: A-G1, A-G2, A-G3, A-G4, A-G5, A-G6 and A-G7:

wherein * denotes the point of attachement of the group A-Gn to the(thio)carbonyl moiety.

In table 1, unless otherwise specified, M+H (Apcl+) means the molecularion peak plus 1 a.m.u. (atomic mass unit) as observed in massspectroscopy via positive atmospheric pressure chemical ionisation.

In table 1, the log P values were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (comprising 3to 16 carbon atoms) with known log P values (determination of the log Pvalues by the retention times using linear interpolation between twosuccessive alkanones). lambda-max-values were determined usingUV-spectra from 200 nm to 400 nm and the peak values of thechromatographic signals.

Table 2 provides the NMR data (¹H) of a selected number of compoundsfrom table 1

TABLE 1 Mass Example A T n Z1 Z2 Z3 Z4 Z5 Z6 Z7 B logP (M + H) NMR 1A-G4 O 0 Me Me H H H phenyl 2.71 321 2 A-G5 O 0 Me Me H H H phenyl 2.92339 3 A-G3 O 0 Me Me H H H phenyl 2.61 305 4 A-G3 O 0 Me Me H Hcyclopropyl phenyl 3.50 345 5 A-G4 O 0 Me Me H H cyclopropyl phenyl 3.44361 6 A-G7 O 0 Me Me H H H phenyl 3.13 308 table 2 7 A-G6 O 0 Me Me H HH phenyl 3.15     362 ⁽¹⁾ 8 A-G5 O 0 Me Me H H cyclopropyl phenyl 3.89379 9 A-G6 O 0 Me Me H H cyclopropyl phenyl 4.13     402 ⁽¹⁾ 10 A-G6 O 0Me Me H H cyclopropyl 2-methylphenyl 4.41     416 ⁽¹⁾ 11 A-G5 O 0 Me MeH H cyclopropyl 2-methylphenyl 4.18 393 12 A-G4 O 0 Me Me H Hcyclopropyl 2-methylphenyl 3.73 375 13 A-G3 O 0 Me Me H H cyclopropyl2-methylphenyl 3.80 359 14 A-G6 O 0 Me Me H H cyclopropyl 2-fluorophenyl4.18     420 ⁽¹⁾ 15 A-G5 O 0 Me Me H H cyclopropyl 2-fluorophenyl 3.96397 16 A-G4 O 0 Me Me H H cyclopropyl 2-fluorophenyl 3.51 379 17 A-G3 O0 Me Me H H cyclopropyl 2-fluorophenyl 3.58 363 18 A-G3 O 0 Me Me H Hcyclopropyl 2-ethylphenyl 4.16 373 19 A-G4 O 0 Me Me H H cyclopropyl2-ethylphenyl 4.06 389 20 A-G5 O 0 Me Me H H cyclopropyl 2-ethylphenyl4.51 407 21 A-G6 O 0 Me Me H H cyclopropyl 2-ethylphenyl 4.77     430⁽¹⁾ 22 A-G4 O 0 Me Me H H H 2-chlorophenyl 3.06 355 23 A-G3 O 0 Me Me HH cyclopropyl 2-chlorophenyl 3.94 379 table 2 24 A-G2 O 0 Me Me H Hcyclopropyl 2-chlorophenyl 5.14 470 table 2 25 A-G1 O 0 Me Me H Hcyclopropyl 2-chlorophenyl 5.03 412 table 2 26 A-G6 O 0 Me Me H Hcyclopropyl 2-chlorophenyl 4.56 (2) table 2 27 A-G5 O 0 Me Me H Hcyclopropyl 2-chlorophenyl 4.31 (2) table 2 28 A-G4 O 0 Me Me H Hcyclopropyl 2-chlorophenyl 3.83 395 table 2 29 A-G4 O 0 Me Me H H H3-chlorophenyl 3.15 355 30 A-G2 O 0 Me Me H H cyclopropyl 3-chlorophenyl5.14 470 table 2 31 A-G1 O 0 Me Me H H cyclopropyl 3-chlorophenyl 5.03412 table 2 32 A-G6 O 0 Me Me H H cyclopropyl 3-chlorophenyl 4.56 (2)table 2 33 A-G5 O 0 Me Me H H cyclopropyl 3-chlorophenyl 4.34 (2) table2 34 A-G4 O 0 Me Me H H cyclopropyl 3-chlorophenyl 3.87 395 table 2 35A-G3 O 0 Me Me H H cyclopropyl 3-chlorophenyl 3.96 (2) table 2 36 A-G4 O0 Me Et H H cyclopropyl 2-chlorophenyl 4.21 409 37 A-G5 O 0 Me Et H Hcyclopropyl 2-chlorophenyl 4.71 427 38 A-G3 O 0 Me Et H H cyclopropyl2-chlorophenyl 4.34 393 39 A-G5 O 0 Me Me H H H 2-chlorophenyl 3.25 37340 A-G3 O 0 Me Me H H H 2-chlorophenyl 2.94 339 41 A-G6 O 0 Me Me H H H2-chlorophenyl 3.50 374 42 A-G7 O 0 Me Me H H H 2-chlorophenyl 3.50 342table 2 43 A-G7 O 0 Me Me H H cyclopropyl 2-chlorophenyl 4.29 382 table2 44 A-G6 O 0 Me Et H H cyclopropyl 2-chlorophenyl 4.95 428 45 A-G4 O 0Me Me H H cyclopropyl 2-chloro- 3.96 413 4-fluorophenyl 46 A-G3 O 0 MeMe H H cyclopropyl 2-chloro- 4.06 397 4-fluorophenyl 47 A-G5 O 0 Me Me HH cyclopropyl 2-chloro- 4.41 431 4-fluorophenyl 48 A-G5 O 0 Me Me H Hcyclopropyl 2-chloro- 4.34 431 5-fluorophenyl 49 A-G6 O 0 Me Me H Hcyclopropyl 2-chloro- 4.59 432 5-fluorophenyl 50 A-G3 O 0 Me Me H Hcyclopropyl 2-chloro- 3.99 397 5-fluorophenyl 51 A-G4 O 0 Me Me H Hcyclopropyl 2-chloro- 3.89 413 5-fluorophenyl 52 A-G6 O 0 Me Me H Hcyclopropyl 2-chloro- 4.67 432 4-fluorophenyl 53 A-G3 O 0 Me Me H Hcyclopropyl 2-(trifluoromethyl) 4.04 413 phenyl 54 A-G6 O 0 Me Me H Hcyclopropyl 2-(trifluoromethyl) 4.61 448 phenyl 55 A-G5 O 0 Me Me H Hcyclopropyl 2-(trifluoromethyl) 4.39 447 phenyl 56 A-G4 O 0 Me Me H Hcyclopropyl 2-(trifluoromethyl) 3.94 429 phenyl 57 A-G4 O 0 Me Me H H H2,4-dichlorophenyl 3.64 389 58 A-G6 O 0 Me Me H H cyclopropyl2,4-dichlorophenyl 5.25 448 table 2 59 A-G3 O 0 Me Me H H cyclopropyl2,4-dichlorophenyl 4.64 413 table 2 60 A-G2 O 0 Me Me H H cyclopropyl2,4-dichlorophenyl 5.88 504 table 2 61 A-G1 O 0 Me Me H H cyclopropyl2,4-dichlorophenyl 5.72 446 table 2 62 A-G4 O 0 Me Me H H cyclopropyl2,4-dichlorophenyl 4.51 429 table 2 63 A-G4 O 0 Me Me H H H3,5-dichlorophenyl 3.69 389 64 A-G6 O 0 Me Me H H cyclopropyl3,5-dichlorophenyl 4.95 448 65 A-G3 O 0 Me Me H H cyclopropyl3,5-dichlorophenyl 4.61 413 table 2 66 A-G1 O 0 Me Me H H cyclopropyl3,5-dichlorophenyl 5.65 446 table 2 67 A-G5 O 0 Me Me H H cyclopropyl3,5-dichlorophenyl 4.95 447 table 2 68 A-G4 O 0 Me Me H H cyclopropyl3,5-dichlorophenyl 4.49 429 table 2 69 A-G3 O 0 Me Me H H cyclopropyl1-naphthyl 4.15 395 table 2 70 A-G2 O 0 Me Me H H cyclopropyl 1-naphthyl5.31 486 table 2 71 A-G1 O 0 Me Me H H cyclopropyl 1-naphthyl 5.19 428table 2 72 A-G6 O 0 Me Me H H cyclopropyl 1-naphthyl 4.77 (2) table 2 73A-G5 O 0 Me Me H H cyclopropyl 1-naphthyl 4.51 (2) table 2 74 A-G4 O 0Me Me H H cyclopropyl 1-naphthyl 4.04 411 table 2 75 A-G3 O 0 Me Me H Hcyclopropyl 2-naphthyl 4.23 395 table 2 76 A-G2 O 0 Me Me H Hcyclopropyl 2-naphthyl 5.36 486 table 2 77 A-G6 O 0 Me Me H Hcyclopropyl 2-naphthyl 4.80 (2) table 2 78 A-G5 O 0 Me Me H Hcyclopropyl 2-naphthyl 4.56 (2) table 2 79 A-G4 O 0 Me Me H Hcyclopropyl 2-naphthyl 4.11 411 table 2 80 A-G1 O 0 Me Me H Hcyclopropyl 2-naphthyl 5.25 (2) table 2 81 A-G5 O 0 Me Me H Hcyclopropyl 2-thienyl 3.80 385 table 2 82 A-G6 O 0 Me Me H H cyclopropyl2-thienyl 4.01 (2) table 2 83 A-G3 O 0 Me Me H H cyclopropyl 2-thienyl3.39 (2) table 2 84 A-G2 O 0 Me Me H H cyclopropyl 2-thienyl 4.59 (2)table 2 85 A-G1 O 0 Me Me H H cyclopropyl 2-thienyl 4.51 (2) table 2 86A-G6 O 0 Me Me H H cyclopropyl 3-thienyl 3.94 386 table 2 87 A-G4 O 0 MeMe H H cyclopropyl 3-thienyl 3.27 367 table 2 88 A-G3 O 0 Me Me H Hcyclopropyl 3-thienyl 3.33 351 table 2 89 A-G2 O 0 Me Me H H cyclopropyl3-thienyl 4.49 442 table 2 90 A-G1 O 0 Me Me H H cyclopropyl 3-thienyl4.44 384 table 2 91 A-G5 O 0 Me Me H H cyclopropyl 3-thienyl 3.72 (2)table 2 92 A-G4 O 1 H H Me Me H H cyclopropyl phenyl 3.80 375 table 2 93A-G6 O 1 H H Me Me H H cyclopropyl phenyl 4.44 394 table 2 94 A-G3 O 1 HH Me Me H H cyclopropyl phenyl 3.87 359 table 2 95 A-G2 O 1 H H Me Me HH cyclopropyl phenyl 5.00 450 table 2 96 A-G1 O 1 H H Me Me H Hcyclopropyl phenyl 4.90 392 table 2 97 A-G5 O 1 H H Me Me H Hcyclopropyl phenyl 4.19 393 table 2 98 A-G4 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 4.11 409 table 2 99 A-G6 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 4.82 428 table 2 100 A-G3 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 4.25 393 table 2 101 A-G2 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 5.45 484 table 2 102 A-G1 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 5.31 426 table 2 103 A-G5 O 1 H H Me Me H Hcyclopropyl 2-chlorophenyl 4.59 427 table 2 104 A-G4 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 4.16 409 table 2 105 A-G6 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 4.82 428 table 2 106 A-G3 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 4.30 393 table 2 107 A-G2 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 5.45 484 table 2 108 A-G1 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 5.31 426 table 2 109 A-G5 O 1 H H Me Me H Hcyclopropyl 3-chlorophenyl 4.61 427 table 2 110 A-G4 O 1 H H Me Me H Hcyclopropyl 2,4-dichlorophenyl 4.74 443 table 2 111 A-G6 O 1 H H Me Me HH cyclopropyl 2,4-dichlorophenyl 5.45 462 table 2 112 A-G3 O 1 H H Me MeH H cyclopropyl 2,4-dichlorophenyl 4.90 427 table 2 113 A-G2 O 1 H H MeMe H H cyclopropyl 2,4-dichlorophenyl 6.14 518 table 2 114 A-G1 O 1 H HMe Me H H cyclopropyl 2,4-dichlorophenyl 5.94 460 table 2 115 A-G5 O 1 HH Me Me H H cyclopropyl 2,4-dichlorophenyl 5.22 461 table 2 116 A-G6 O 1H H Me Me H H cyclopropyl 3,5-dichlorophenyl 5.45 462 table 2 117 A-G4 O1 H H Me Me H H cyclopropyl 3,5-dichlorophenyl 4.77 443 table 2 118 A-G3O 1 H H Me Me H H cyclopropyl 3,5-dichlorophenyl 4.92 427 table 2 119A-G2 O 1 H H Me Me H H cyclopropyl 3,5-dichlorophenyl 6.14 518 table 2120 A-G1 O 1 H H Me Me H H cyclopropyl 3,5-dichlorophenyl 5.94 460 table2 121 A-G5 O 1 H H Me Me H H cyclopropyl 3,5-dichlorophenyl 5.22 461table 2 122 A-G4 O 0 Me Me H H methyl 3,5-dichlorophenyl 403    3.92 123A-G4 S 0 Me Me H H H 2-chlorophenyl 371    3.83 124 A-G4 S 0 Me Me H Hcyclopropyl 2,4-dichlorophenyl 445    5.13 125 A-G4 S 0 Me Me H Hcyclopropyl 2-naphthyl 427    4.72 126 A-G6 S 0 Me Me H H cyclopropyl2-naphthyl 446    5.35 127 A-G4 S 1 H H Me Me H H cyclopropyl2-chlorophenyl 425    4.76 Note ⁽¹⁾ M + Na ion Note (2): loss of aryl;fragment [Si(Me)₂CH₂N(cPr)C(═O)A] Note: Me: methyl; Et: ethyl

TABLE 2 NMR peak lists The ¹H-NMR data (at 400 Mhz in DMSO-d₆) ofselected examples are stated in the form of ¹H-NMR peak lists. For eachsignal peak, the δ value in ppm and the signal intensity in brackets arelisted: Example ¹H-NMR (400 Mhz in DMSO-d₆) 6 7.6222 (0.43); 7.5496(0.90); 7.5449 (1.18); 7.5385 (0.68); 7.5327 (0.90); 7.5259 (1.24);7.3855 (0.38); 7.3765 (1.82); 7.3734 (1.84); 7.3671 (0.68); 7.3612(0.89); 7.3588 (1.02); 4.2149 (1.03); 4.2067 (0.80); 4.2037 (1.09);4.2004 (0.79); 4.1923 (1.06); 3.3460 (13.28); 2.9830 (1.06); 2.9748(0.78); 2.9717 (1.10); 2.9604 (1.01); 2.8651 (1.95); 2.8507 (1.94);2.5166 (2.47); 2.5122 (5.04); 2.5078 (6.77); 2.5033 (4.82); 2.4990(2.24); 1.8778 (7.97); 0.2935 (0.78); 0.2854 (16.00); 0.2771 (0.71) 238.4477 (0.90); 8.4429 (0.97); 8.4357 (0.93); 8.4309 (0.92); 7.7708(0.84); 7.7661 (0.87); 7.7519 (1.00); 7.7471 (0.96); 7.5733 (0.87);7.5556 (0.91); 7.4954 (1.02); 7.4834 (0.98); 7.4764 (0.94); 7.4644(0.90); 7.4486 (1.83); 7.4398 (2.19); 7.4361 (1.14); 7.3822 (0.63);7.3717 (0.70); 7.3638 (0.59); 7.3612 (0.49); 7.3553 (0.52); 7.3514(0.44); 7.3426 (0.34); 3.3903 (0.52); 3.3721 (0.77); 3.3371 (66.23);2.6028 (0.32); 2.5953 (0.38); 2.5860 (0.62); 2.5761 (0.42); 2.5684(0.35); 2.5252 (0.44); 2.5116 (7.50); 2.5074 (14.80); 2.5029 (19.60);2.4984 (14.69); 2.4944 (7.46); 1.2309 (0.42); 0.5093 (16.00); 0.4637(0.70); 0.4533 (0.85); 0.4455 (1.04); 0.3840 (0.86); 0.3742 (0.73);0.3667 (0.85); 0.3570 (0.65); 0.1189 (0.89); −0.0002 (0.97) 24 7.8593(1.09); 7.8409 (1.07); 7.5830 (0.95); 7.5658 (0.90); 7.5638 (0.87);7.4486 (1.91); 7.4461 (2.03); 7.4388 (1.73); 7.4364 (1.57); 7.4322(1.27); 7.4276 (0.70); 7.4161 (0.43); 7.4112 (1.27); 7.4086 (1.17);7.3922 (0.76); 7.3900 (0.75); 7.3795 (0.73); 7.3709 (0.59); 7.3667(0.53); 7.3612 (0.73); 7.3583 (0.59); 7.3538 (0.62); 7.3474 (0.49);7.3400 (0.42); 7.1380 (0.49); 7.1340 (0.67); 7.1190 (0.73); 7.1147(1.31); 7.1099 (1.25); 7.0997 (0.42); 7.0956 (0.77); 7.0912 (1.11);3.3713 (0.36); 3.3529 (0.57); 3.3306 (58.18); 2.5997 (0.38); 2.5918(0.44); 2.5824 (0.68); 2.5729 (0.47); 2.5649 (0.37); 2.5245 (0.47);2.5110 (8.87); 2.5067 (17.50); 2.5021 (23.09); 2.4976 (17.19); 2.4933(8.61); 1.2302 (0.50); 0.5197 (16.00); 0.4631 (1.32); 0.4566 (1.21);0.4541 (1.21); 0.4456 (1.18); 0.4203 (0.40); 0.3558 (0.60); 0.3408(0.84); 0.3320 (0.63); 0.3202 (0.49); 0.1290 (0.94); −0.0002 (1.66) 257.7876 (1.07); 7.7681 (1.31); 7.6986 (0.50); 7.6805 (1.12); 7.6619(0.80); 7.6256 (0.89); 7.6064 (1.10); 7.5871 (0.50); 7.5785 (1.35);7.5612 (1.19); 7.5593 (1.16); 7.4559 (2.51); 7.4534 (2.63); 7.4454(2.20); 7.4399 (1.46); 7.4236 (0.39); 7.4200 (0.40); 7.3856 (0.92);7.3767 (0.76); 7.3731 (0.70); 7.3673 (0.89); 7.3644 (0.66); 7.3597(0.66); 7.3538 (0.61); 7.3462 (0.61); 7.3217 (1.21); 7.3029 (1.06);5.2982 (0.34); 3.3896 (0.36); 3.3718 (0.74); 3.3378 (121.27); 2.5618(0.44); 2.5561 (0.53); 2.5460 (0.84); 2.5254 (0.93); 2.5118 (13.36);2.5074 (26.19); 2.5028 (34.54); 2.4983 (25.58); 2.4940 (12.67); 1.2307(0.69); 0.4999 (16.00); 0.4592 (1.02); 0.4456 (1.56); 0.4411 (0.54);0.4318 (0.33); 0.4159 (0.37); 0.4096 (0.38); 0.4008 (0.58); 0.3900(0.37); 0.3760 (0.36); 0.3645 (0.39); 0.3563 (0.59); 0.3475 (0.42);0.3410 (0.51); 0.3319 (0.35); 0.3240 (0.36); 0.3052 (0.48); 0.3015(0.54); 0.2420 (0.35); 0.1099 (1.03); −0.0002 (3.64) 26 9.0491 (1.20);9.0434 (1.35); 8.9566 (1.34); 8.9509 (1.22); 7.5668 (0.87); 7.5491(0.89); 7.4574 (1.79); 7.4556 (1.75); 7.4479 (1.65); 7.4420 (1.00);7.3890 (0.59); 7.3800 (0.50); 7.3766 (0.44); 7.3705 (0.58); 7.3631(0.42); 7.3570 (0.41); 3.4348 (1.48); 3.3351 (54.80); 2.5831 (0.35);2.5736 (0.60); 2.5630 (0.39); 2.5561 (0.36); 2.5075 (12.96); 2.5032(17.01); 2.4988 (12.98); 0.5129 (0.97); 0.5044 (16.00); 0.4797 (0.65);0.4417 (0.49); 0.3992 (1.00); 0.3742 (1.13); 0.3631 (0.81); 0.3565(0.98) 27 8.7910 (0.89); 8.7804 (0.90); 7.8706 (0.74); 7.8512 (1.03);7.7707 (0.87); 7.7591 (0.86); 7.7510 (0.64); 7.7393 (0.62); 7.5773(0.96); 7.5592 (1.00); 7.4559 (2.06); 7.4468 (2.10); 7.4427 (1.18);7.3874 (0.65); 7.3778 (0.57); 7.3759 (0.54); 7.3689 (0.63); 7.3611(0.48); 7.3558 (0.49); 7.3478 (0.35); 3.3325 (53.29); 2.5683 (0.39);2.5567 (0.63); 2.5431 (0.44); 2.5250 (0.44); 2.5112 (7.23); 2.5071(14.19); 2.5027 (18.85); 2.4983 (14.39); 0.5004 (16.00); 0.4155 (0.43);0.3894 (0.58); −0.0002 (0.38); −0.0490 (0.50) 28 8.7275 (0.70); 8.7241(0.75); 8.7156 (0.78); 8.7123 (0.78); 7.8113 (0.64); 7.7915 (0.77);7.6121 (0.55); 7.6005 (0.57); 7.5925 (0.52); 7.5804 (1.24); 7.5627(0.83); 7.4555 (1.70); 7.4467 (1.66); 7.4422 (0.97); 7.3864 (0.55);7.3770 (0.49); 7.3680 (0.55); 7.3602 (0.41); 7.3547 (0.37); 6.9437(0.58); 6.8086 (1.26); 6.6736 (0.62); 3.3794 (2.14); 3.3300 (183.46);3.3015 (0.44); 2.6710 (0.59); 2.6666 (0.42); 2.6610 (0.41); 2.6539(0.36); 2.6437 (0.59); 2.6330 (0.37); 2.6284 (0.37); 2.5240 (1.50);2.5106 (26.97); 2.5063 (53.21); 2.5018 (70.51); 2.4973 (53.08); 2.4932(27.20); 2.3286 (0.43); 1.2353 (0.56); 0.5033 (16.00); 0.3901 (1.92);0.3724 (0.99); −0.0002 (1.49) 30 7.8540 (0.86); 7.8520 (0.92); 7.8342(0.93); 7.8322 (0.94); 7.6105 (1.06); 7.6055 (1.04); 7.5815 (0.49);7.5784 (0.70); 7.5754 (0.49); 7.5643 (0.63); 7.5612 (0.84); 7.5585(0.62); 7.4793 (0.42); 7.4741 (0.35); 7.4632 (0.92); 7.4584 (1.26);7.4541 (0.85); 7.4466 (1.14); 7.4293 (0.97); 7.4082 (0.65); 7.4050(0.53); 7.3887 (0.96); 7.3862 (1.00); 7.3699 (0.63); 7.3674 (0.70);7.1298 (0.48); 7.1258 (0.55); 7.1104 (0.76); 7.1066 (0.82); 7.0914(0.42); 7.0874 (0.44); 6.9795 (0.81); 6.9757 (0.81); 6.9605 (0.78);6.9567 (0.72); 3.3530 (0.47); 3.3303 (49.09); 2.9756 (0.39); 2.5640(0.37); 2.5547 (0.59); 2.5447 (0.44); 2.5370 (0.38); 2.5248 (0.47);2.5111 (7.37); 2.5067 (14.51); 2.5021 (19.16); 2.4976 (14.31); 2.4932(7.18); 1.2302 (0.43); 0.4553 (1.03); 0.4473 (16.00); 0.4390 (1.34);0.3757 (0.33); 0.3466 (0.68); 0.3317 (1.58); 0.2956 (0.32); −0.0002(1.30) 31 7.7804 (0.83); 7.7614 (1.02); 7.6741 (0.34); 7.6559 (0.88);7.6377 (0.70); 7.6161 (0.76); 7.6062 (1.38); 7.6008 (1.77); 7.5764(1.07); 7.5592 (1.05); 7.4873 (0.46); 7.4823 (0.36); 7.4711 (0.98);7.4668 (1.38); 7.4622 (0.88); 7.4531 (1.49); 7.4356 (1.18); 7.4158(0.49); 7.1808 (0.93); 7.1622 (0.85); 3.3723 (0.37); 3.3345 (70.37);2.5249 (0.79); 2.5115 (9.51); 2.5073 (17.79); 2.5028 (23.39); 2.4984(17.65); 1.2311 (0.45); 0.4275 (16.00); 0.3906 (0.48); 0.3454 (0.44);0.3319 (1.48); 0.3236 (0.34); 0.3174 (0.32); 0.3056 (0.47); 0.2961(0.51); 0.2864 (0.52); 0.2761 (0.37); 0.2548 (0.35); 0.2396 (0.32);−0.0002 (1.26) 32 9.0396 (1.15); 9.0338 (1.32); 8.9527 (1.30); 8.9468(1.18); 7.6165 (1.14); 7.6121 (1.13); 7.5742 (0.72); 7.5572 (0.90);7.4767 (0.40); 7.4607 (0.78); 7.4563 (1.16); 7.4518 (0.69); 7.4451(1.27); 7.4277 (1.03); 7.4080 (0.38); 3.3301 (42.10); 3.2926 (1.57);2.5655 (0.34); 2.5535 (0.60); 2.5382 (0.42); 2.5254 (0.49); 2.5113(6.52); 2.5072 (12.98); 2.5027 (17.38); 2.4983 (13.28); 0.4326 (0.86);0.4245 (16.00); 0.3930 (1.75); 0.3852 (2.03); 0.3677 (1.11); −0.0002(0.47) 33 8.7874 (0.62); 8.7808 (0.93); 8.7721 (0.69); 7.7407 (1.61);7.7366 (1.67); 7.7309 (3.20); 7.6088 (1.21); 7.6040 (1.23); 7.5765(0.79); 7.5595 (0.99); 7.4884 (0.42); 7.4723 (0.85); 7.4677 (1.19);7.4633 (0.73); 7.4543 (1.33); 7.4367 (1.08); 7.4172 (0.44); 3.3285(33.97); 2.5367 (0.44); 2.5214 (0.90); 2.5112 (6.82); 2.5070 (13.24);2.5026 (17.55); 2.4981 (13.50); 0.4284 (16.00); 0.3989 (0.63); −0.0002(0.54) 34 8.7203 (0.76); 8.7170 (0.84); 8.7087 (0.83); 8.7053 (0.84);7.6992 (0.64); 7.6797 (0.90); 7.6098 (1.19); 7.6053 (1.21); 7.5958(0.71); 7.5813 (0.91); 7.5776 (1.18); 7.5614 (1.16); 7.4873 (0.42);7.4712 (0.81); 7.4666 (1.16); 7.4623 (0.73); 7.4525 (1.21); 7.4349(1.02); 7.4152 (0.40); 6.8843 (0.62); 6.7493 (1.35); 6.6143 (0.68);3.3269 (24.49); 3.2492 (2.03); 2.6294 (0.46); 2.6162 (0.60); 2.6019(0.45); 2.5109 (5.93); 2.5067 (11.90); 2.5022 (15.94); 2.4978 (12.15);0.4333 (16.00); 0.3887 (2.54); 0.3748 (3.83); −0.0002 (0.56) 35 8.4425(0.81); 8.4378 (0.89); 8.4306 (0.89); 8.4258 (0.88); 7.6830 (0.78);7.6782 (0.83); 7.6641 (0.97); 7.6593 (0.95); 7.6105 (1.16); 7.6066(1.16); 7.5744 (0.74); 7.5572 (0.91); 7.4841 (1.13); 7.4799 (0.49);7.4723 (1.06); 7.4641 (1.29); 7.4587 (1.21); 7.4536 (1.32); 7.4462(1.23); 7.4288 (1.00); 7.4090 (0.39); 3.3247 (16.41); 3.2445 (0.74);2.5794 (0.33); 2.5705 (0.64); 2.5595 (0.38); 2.5525 (0.32); 2.5065(11.05); 2.5020 (14.64); 2.4976 (11.16); 0.4351 (16.00); 0.3851 (0.91);0.3683 (0.81); −0.0002 (0.72) 42 7.6761 (0.46); 7.5108 (0.53); 7.5091(0.58); 7.5074 (0.52); 7.4944 (0.53); 7.4918 (0.91); 7.4891 (0.58);7.4286 (0.71); 7.4243 (1.30); 7.4156 (2.04); 7.4131 (1.76); 7.3519(0.55); 7.3435 (0.45); 7.3391 (0.42); 7.3337 (0.49); 7.3307 (0.41);7.3239 (0.38); 7.3222 (0.40); 4.2161 (1.04); 4.2079 (0.82); 4.2048(1.10); 4.2015 (0.82); 4.1935 (1.07); 3.3456 (27.34); 3.0009 (1.89);2.9865 (2.15); 2.9753 (0.85); 2.9720 (1.15); 2.9691 (0.85); 2.9607(1.04); 2.5166 (4.24); 2.5123 (8.65); 2.5078 (11.68); 2.5033 (8.36);2.4989 (3.92); 1.8931 (8.19); 0.3822 (0.78); 0.3739 (16.00); 0.3655(0.74) 43 7.4614 (1.01); 7.4589 (0.80); 7.4435 (1.24); 7.4408 (1.01);7.3825 (2.51); 7.3738 (3.06); 7.3708 (1.83); 7.3153 (0.87); 7.3046(1.15); 7.2971 (0.79); 7.2941 (0.67); 7.2874 (0.67); 7.2857 (0.63);7.2759 (0.46); 4.1909 (1.36); 4.1797 (1.59); 4.1765 (1.32); 4.1685(1.52); 3.3516 (0.51); 3.3008 (38.44); 3.1675 (1.68); 2.9567 (1.38);2.9454 (1.57); 2.9343 (1.44); 2.6325 (0.44); 2.6279 (0.45); 2.4813(0.46); 2.4725 (5.96); 2.4681 (12.70); 2.4636 (17.69); 2.4591 (13.34);2.4548 (6.95); 1.6259 (12.81); 0.6455 (1.11); 0.6281 (1.66); 0.3579(16.00) 58 9.0434 (1.18); 9.0376 (1.31); 8.9572 (1.34); 8.9515 (1.20);7.6217 (1.55); 7.6169 (1.67); 7.5662 (1.31); 7.5460 (1.93); 7.4737(1.20); 7.4689 (1.14); 7.4536 (0.79); 7.4488 (0.78); 5.3030 (0.65);3.4101 (1.53); 3.3921 (0.41); 3.3736 (0.80); 3.3554 (0.97); 3.3300(40.04); 2.5848 (0.33); 2.5737 (0.57); 2.5575 (0.45); 2.5446 (0.37);2.5252 (0.55); 2.5114 (10.61); 2.5073 (20.67); 2.5028 (27.24); 2.4983(20.32); 1.2497 (0.59); 1.2316 (1.29); 1.2134 (0.55); 0.5075 (1.23);0.4988 (16.00); 0.4772 (0.65); 0.4456 (0.72); 0.4409 (1.49); 0.3956(1.79); 0.3769 (1.06); 0.3560 (0.54); 0.3386 (0.42); 0.2447 (0.46);−0.0002 (3.12) 59 8.4516 (0.99); 8.4470 (1.01); 8.4396 (1.01); 8.4350(0.96); 7.8043 (0.92); 7.7996 (0.93); 7.7854 (1.07); 7.7807 (1.00);7.6111 (1.66); 7.6063 (1.71); 7.5745 (1.48); 7.5543 (1.90); 7.5016(1.05); 7.4896 (1.05); 7.4827 (1.00); 7.4706 (1.13); 7.4662 (1.36);7.4615 (1.18); 7.4461 (0.89); 7.4414 (0.84); 3.3903 (0.38); 3.3726(0.74); 3.3350 (63.44); 2.9982 (0.39); 2.6159 (0.36); 2.6087 (0.42);2.5998 (0.70); 2.5897 (0.46); 2.5818 (0.38); 2.5076 (16.46); 2.5033(21.14); 2.4989 (15.98); 1.2317 (0.52); 0.5022 (16.00); 0.4662 (0.86);0.4491 (0.73); 0.4414 (2.02); 0.4012 (1.10); 0.3845 (1.02); 0.3563(0.34); 0.2524 (0.67); −0.0002 (0.34) 60 7.8626 (1.03); 7.8603 (1.06);7.8416 (1.22); 7.6083 (1.71); 7.6036 (1.83); 7.5862 (1.52); 7.5661(2.06); 7.4596 (1.23); 7.4547 (1.21); 7.4392 (1.20); 7.4348 (1.46);7.4183 (1.22); 7.3995 (0.70); 7.3976 (0.65); 7.1395 (1.01); 7.1358(1.32); 7.1319 (1.11); 7.1210 (1.21); 7.1172 (1.34); 7.1128 (0.96);7.1044 (0.67); 7.1006 (0.43); 3.3538 (0.36); 3.3275 (30.71); 2.9762(0.33); 2.6149 (0.39); 2.6071 (0.49); 2.5978 (0.73); 2.5884 (0.49);2.5802 (0.39); 2.5249 (0.40); 2.5071 (13.87); 2.5026 (18.18); 2.4982(13.60); 1.2314 (0.40); 0.5126 (16.00); 0.4669 (1.41); 0.4595 (1.33);0.4409 (2.09); 0.4157 (0.39); 0.3563 (0.98); 0.3505 (0.80); 0.3392(0.66); 0.2733 (0.40); −0.0002 (1.50) 61 7.7897 (1.04); 7.7705 (1.30);7.7080 (0.46); 7.6901 (1.11); 7.6715 (0.78); 7.6317 (0.82); 7.6165(2.71); 7.6118 (3.27); 7.5938 (0.51); 7.5772 (1.88); 7.5711 (0.33);7.5571 (2.52); 7.4672 (1.66); 7.4623 (1.53); 7.4471 (1.18); 7.4422(1.10); 7.3586 (1.18); 7.3396 (1.04); 3.3722 (0.35); 3.3539 (0.43);3.3481 (0.36); 3.3272 (57.54); 2.5759 (0.45); 2.5657 (0.72); 2.5526(0.51); 2.5377 (0.34); 2.5247 (0.70); 2.5113 (12.34); 2.5069 (24.59);2.5024 (32.72); 2.4979 (24.45); 2.4935 (12.29); 1.2309 (0.61); 0.4915(16.00); 0.4618 (0.54); 0.4491 (0.58); 0.4407 (2.09); 0.4325 (0.49);0.4058 (0.34); 0.3954 (0.46); 0.3764 (0.34); 0.3724 (0.35); 0.3646(0.35); 0.3559 (0.66); 0.3510 (0.42); 0.3386 (0.62); 0.3320 (0.40);0.3140 (0.39); 0.3038 (0.55); 0.2394 (0.59); −0.0002 (2.77) 62 8.7332(0.80); 8.7301 (0.86); 8.7215 (0.87); 8.7183 (0.86); 7.8587 (0.73);7.8392 (0.85); 7.6194 (1.79); 7.6144 (1.96); 7.6035 (0.59); 7.5915(0.56); 7.5807 (1.29); 7.5606 (1.79); 7.4692 (1.09); 7.4644 (1.06);7.4491 (0.80); 7.4442 (0.77); 6.9483 (0.64); 6.8132 (1.39); 6.6780(0.70); 3.3518 (2.59); 3.3307 (50.72); 2.6768 (0.45); 2.6714 (0.43);2.6647 (0.65); 2.6505 (0.42); 2.5251 (0.39); 2.5114 (7.70); 2.5071(15.27); 2.5026 (20.25); 2.4981 (15.23); 2.4941 (7.82); 0.4958 (16.00);0.4041 (3.30); 0.3886 (1.68); −0.0002 (0.39) 65 8.4499 (0.87); 8.4451(0.92); 8.4379 (0.92); 8.4331 (0.89); 7.7567 (0.83); 7.7519 (0.85);7.7378 (0.99); 7.7330 (0.95); 7.6369 (0.71); 7.6321 (1.56); 7.6273(1.10); 7.5916 (3.83); 7.5867 (3.16); 7.4982 (1.03); 7.4862 (0.97);7.4793 (0.88); 7.4673 (0.84); 3.3281 (36.81); 3.2351 (0.40); 2.5987(0.60); 2.5880 (0.36); 2.5249 (0.38); 2.5115 (7.25); 2.5071 (14.18);2.5026 (18.66); 2.4981 (13.79); 2.4938 (6.84); 1.2312 (0.38); 0.4496(1.30); 0.4415 (16.00); 0.4040 (0.90); 0.3867 (0.84); 0.3768 (0.54);0.3643 (1.36); −0.0002 (1.32) 66 7.7870 (0.81); 7.7678 (1.00); 7.6981(0.35); 7.6798 (0.87); 7.6612 (0.65); 7.6406 (0.91); 7.6357 (1.84);7.6308 (1.60); 7.6091 (0.84); 7.5853 (4.25); 7.5804 (3.53); 7.2838(0.90); 7.2651 (0.81); 3.3540 (0.33); 3.3250 (29.71); 2.5673 (0.32);2.5616 (0.37); 2.5515 (0.62); 2.5389 (0.47); 2.5112 (9.41); 2.5068(18.44); 2.5023 (24.27); 2.4978 (17.92); 2.4935 (8.88); 1.2309 (0.45);0.4325 (16.00); 0.3904 (0.42); 0.3717 (0.61); 0.3642 (1.69); 0.3458(0.46); 0.3371 (0.36); 0.3279 (0.55); 0.3047 (0.37); 0.2999 (0.49);0.2688 (0.34); −0.0002 (2.55) 67 8.7939 (0.80); 8.7827 (0.83); 7.8583(0.64); 7.8389 (0.97); 7.7760 (0.82); 7.7643 (0.81); 7.7562 (0.57);7.7446 (0.54); 7.6416 (0.75); 7.6368 (1.63); 7.6320 (1.09); 7.5902(3.93); 7.5853 (3.44); 3.3342 (62.03); 2.5728 (0.38); 2.5600 (0.59);2.5464 (0.43); 2.5254 (0.41); 2.5117 (7.42); 2.5076 (14.82); 2.5031(19.84); 2.4987 (15.19); 0.4336 (16.00); 0.4063 (0.72); 0.4004 (0.73);−0.0002 (0.35) 68 8.7300 (0.80); 8.7272 (0.88); 8.7185 (0.88); 8.7155(0.89); 7.8013 (0.74); 7.7823 (0.90); 7.6417 (0.76); 7.6369 (1.68);7.6321 (1.20); 7.6179 (0.65); 7.6059 (0.69); 7.5926 (3.93); 7.5877(3.77); 6.9079 (0.64); 6.7728 (1.37); 6.6377 (0.69); 3.3317 (54.71);3.2345 (2.55); 2.6727 (0.60); 2.6594 (0.75); 2.6458 (0.52); 2.5071(14.98); 2.5027 (20.21); 2.4982 (15.64); 0.4391 (16.00); 0.4044 (3.75);0.3906 (3.65); 0.3642 (0.63); −0.0002 (0.34) 69 8.4351 (0.93); 8.4303(1.01); 8.4231 (1.02); 8.4183 (1.01); 8.2028 (0.87); 8.1821 (0.94);8.0097 (0.91); 7.9873 (1.46); 7.9658 (0.93); 7.9629 (0.93); 7.7831(0.86); 7.7805 (0.89); 7.7661 (1.07); 7.7635 (1.00); 7.6301 (1.09);7.6255 (1.28); 7.6114 (1.80); 7.6069 (1.63); 7.5913 (0.67); 7.5874(0.60); 7.5719 (0.69); 7.5691 (0.74); 7.5528 (1.65); 7.5355 (1.27);7.5329 (1.36); 7.5158 (0.81); 7.4635 (1.10); 7.4515 (1.10); 7.4446(0.93); 7.4326 (0.93); 3.4824 (1.26); 3.3775 (0.32); 3.3441 (66.02);2.8967 (0.52); 2.7381 (0.43); 2.5315 (0.50); 2.5178 (7.90); 2.5136(15.20); 2.5090 (20.07); 2.5045 (15.03); 2.5002 (7.70); 1.2369 (0.36);0.6246 (16.00); 0.4274 (1.08); 0.2758 (0.54) 70 8.1833 (0.88); 8.1626(0.93); 8.0013 (0.92); 7.9802 (1.73); 7.9594 (0.93); 7.9570 (0.92);7.8446 (1.07); 7.8251 (1.10); 7.7851 (0.84); 7.7829 (0.89); 7.7682(1.02); 7.7662 (0.98); 7.6222 (0.34); 7.6190 (0.39); 7.6052 (0.68);7.6019 (0.82); 7.5848 (0.63); 7.5811 (0.57); 7.5616 (0.73); 7.5467(1.41); 7.5269 (1.36); 7.5096 (0.79); 7.3751 (0.55); 7.3563 (1.14);7.3374 (0.65); 7.1151 (0.50); 7.1112 (0.55); 7.0957 (0.87); 7.0920(0.90); 7.0766 (0.50); 7.0728 (0.47); 6.9377 (0.90); 6.9340 (0.91);6.9187 (0.87); 6.9150 (0.81); 3.3290 (43.30); 2.8899 (0.56); 2.7310(0.48); 2.5242 (0.63); 2.5105 (8.42); 2.5065 (16.18); 2.5021 (21.03);2.4976 (16.13); 2.4935 (8.21); 2.4811 (0.66); 0.6288 (16.00); 0.5958(0.32); 0.4206 (1.37); 0.4129 (1.26); 0.2452 (0.46); −0.0002 (1.60) 718.1838 (1.25); 8.1630 (1.29); 8.0106 (1.29); 7.9872 (1.67); 7.9655(1.29); 7.9625 (1.23); 7.7847 (1.25); 7.7820 (1.32); 7.7680 (2.18);7.7544 (1.30); 7.7505 (1.15); 7.6346 (0.42); 7.6168 (1.52); 7.6005(2.66); 7.5966 (2.31); 7.5827 (1.68); 7.5790 (1.78); 7.5651 (1.18);7.5624 (1.40); 7.5539 (1.56); 7.5453 (1.41); 7.5367 (1.47); 7.5335(1.50); 7.5285 (0.71); 7.5260 (0.63); 7.5164 (1.13); 7.1127 (1.12);7.0953 (1.01); 3.3536 (0.37); 3.3298 (58.47); 2.5249 (0.58); 2.5115(10.80); 2.5071 (21.35); 2.5025 (28.25); 2.4980 (20.99); 2.4936 (10.45);2.4767 (0.57); 2.4693 (0.58); 2.4594 (0.84); 2.4493 (0.54); 2.4427(0.46); 1.2307 (0.45); 0.6121 (16.00); 0.5828 (0.47); 0.5716 (0.45);0.5125 (0.36); 0.4215 (0.56); 0.2550 (0.32); 0.2144 (0.39); 0.2041(0.39); −0.0002 (1.70) 72 9.0612 (1.26); 9.0553 (1.43); 8.9622 (1.41);8.9563 (1.29); 8.1984 (0.88); 8.1778 (0.94); 8.0053 (0.92); 7.9836(1.62); 7.9604 (0.91); 7.7717 (0.87); 7.7697 (0.88); 7.7549 (1.04);7.6346 (0.35); 7.6316 (0.38); 7.6174 (0.66); 7.6143 (0.81); 7.5970(0.60); 7.5936 (0.55); 7.5700 (0.70); 7.5514 (1.72); 7.5337 (1.27);7.5136 (0.70); 3.5154 (0.98); 3.3369 (58.51); 2.8914 (0.32); 2.6019(0.32); 2.5946 (0.38); 2.5852 (0.63); 2.5754 (0.43); 2.5676 (0.36);2.5256 (0.39); 2.5121 (7.23); 2.5080 (14.09); 2.5036 (18.58); 2.4992(14.00); 0.6115 (16.00); 0.5942 (0.66); 0.3644 (0.84); 0.2908 (0.98);0.2814 (0.68); 0.2735 (0.97) 73 8.7704 (0.92); 8.7599 (0.93); 8.1795(1.01); 8.1588 (1.07); 8.0133 (1.05); 7.9923 (1.25); 7.9672 (1.04);7.9649 (1.03); 7.7838 (0.97); 7.7816 (1.02); 7.7669 (1.17); 7.7648(1.14); 7.7202 (0.55); 7.7087 (0.54); 7.7005 (1.03); 7.6889 (1.05);7.6535 (1.28); 7.6360 (0.66); 7.6230 (0.40); 7.6196 (0.44); 7.6058(0.80); 7.6026 (0.93); 7.5855 (0.73); 7.5817 (0.66); 7.5677 (0.78);7.5654 (0.85); 7.5553 (1.13); 7.5479 (1.10); 7.5380 (1.18); 7.5351(1.26); 7.5179 (0.87); 3.3333 (54.12); 2.5249 (0.40); 2.5074 (16.18);2.5029 (21.45); 2.4985 (16.35); 2.4735 (0.76); 2.4622 (0.46); 0.6132(16.00); 0.4145 (0.80); 0.3034 (0.49); −0.0003 (0.33) 74 8.7020 (0.79);8.6981 (0.86); 8.6906 (0.87); 8.6867 (0.85); 8.1820 (0.90); 8.1614(0.94); 8.0129 (0.93); 7.9921 (1.09); 7.9663 (0.91); 7.9640 (0.90);7.7844 (0.89); 7.7696 (1.03); 7.7675 (1.00); 7.6181 (0.34); 7.6149(0.38); 7.6008 (0.72); 7.5977 (0.87); 7.5936 (0.77); 7.5808 (0.75);7.5721 (1.24); 7.5692 (1.23); 7.5533 (1.40); 7.5375 (1.63); 7.5338(1.34); 7.5169 (0.94); 6.9097 (0.64); 6.7746 (1.39); 6.6397 (0.70);3.4837 (1.48); 3.3326 (47.22); 2.8904 (0.38); 2.7316 (0.33); 2.5650(0.34); 2.5582 (0.40); 2.5492 (0.69); 2.5385 (0.49); 2.5309 (0.46);2.5201 (0.73); 2.5112 (7.17); 2.5071 (14.20); 2.5027 (18.96); 2.4982(14.42); 0.6156 (16.00); 0.3522 (1.20); 0.3204 (0.54); 0.3093 (1.12);0.2924 (1.02); 0.2836 (0.63) 75 8.4140 (0.98); 8.4093 (1.06); 8.4020(1.07); 8.3973 (1.06); 8.1805 (1.87); 7.9698 (0.62); 7.9567 (0.66);7.9410 (1.27); 7.9205 (1.69); 7.9138 (0.79); 7.9007 (0.86); 7.7346(1.13); 7.7326 (1.11); 7.7144 (0.95); 7.7121 (0.94); 7.6103 (0.94);7.6055 (0.99); 7.5914 (1.18); 7.5866 (1.13); 7.5539 (1.44); 7.5488(1.01); 7.5423 (1.33); 7.5349 (0.98); 7.5303 (1.39); 7.4084 (1.13);7.3964 (1.11); 7.3895 (0.98); 7.3775 (0.95); 3.3380 (62.85); 2.5800(0.36); 2.5726 (0.41); 2.5633 (0.68); 2.5532 (0.47); 2.5456 (0.41);2.5256 (0.43); 2.5121 (7.25); 2.5078 (14.26); 2.5033 (18.87); 2.4988(14.09); 2.4945 (7.09); 0.5196 (16.00); 0.4484 (0.69); 0.4231 (0.41);0.4147 (1.43); 0.3776 (0.37); 0.3535 (0.79); 0.3372 (0.79); 0.3286(0.87) 76 8.1950 (2.43); 7.9787 (0.87); 7.9658 (0.91); 7.9550 (0.96);7.9422 (1.55); 7.9215 (2.21); 7.9022 (1.23); 7.8865 (0.32); 7.8351(1.43); 7.8336 (1.49); 7.8155 (1.52); 7.8138 (1.53); 7.7427 (1.48);7.7408 (1.49); 7.7225 (1.24); 7.7203 (1.26); 7.5652 (0.37); 7.5533(1.98); 7.5482 (1.37); 7.5423 (1.73); 7.5406 (1.70); 7.5346 (1.39);7.5299 (1.94); 7.5179 (0.44); 7.2974 (0.70); 7.2951 (0.71); 7.2786(1.53); 7.2763 (1.53); 7.2599 (0.93); 7.2575 (0.91); 7.0936 (0.75);7.0897 (0.81); 7.0742 (1.18); 7.0705 (1.23); 7.0552 (0.63); 7.0513(0.63); 6.8952 (1.29); 6.8914 (1.32); 6.8762 (1.23); 6.8724 (1.18);3.3724 (0.35); 3.3530 (6.40); 2.5552 (0.45); 2.5474 (0.58); 2.5380(0.86); 2.5284 (0.66); 2.5174 (1.60); 2.5129 (2.97); 2.5084 (3.92);2.5039 (2.90); 2.4997 (1.48); 1.2329 (0.43); 0.5381 (16.00); 0.4757(0.34); 0.4318 (1.58); 0.4192 (2.63); 0.3849 (0.47); 0.3394 (0.68);0.2954 (0.70) 77 9.0269 (1.24); 9.0211 (1.48); 8.9469 (1.41); 8.9411(1.27); 8.1832 (1.80); 7.9756 (0.58); 7.9606 (0.58); 7.9519 (0.69);7.9414 (1.16); 7.9204 (1.81); 7.9112 (0.61); 7.8960 (0.70); 7.7341(1.09); 7.7137 (0.91); 7.5521 (1.57); 7.5462 (0.88); 7.5421 (0.96);7.5388 (0.99); 7.5347 (0.87); 7.5285 (1.51); 3.3806 (1.32); 3.3331(47.92); 2.5892 (0.35); 2.5802 (0.66); 2.5695 (0.41); 2.5622 (0.35);2.5248 (0.34); 2.5074 (13.29); 2.5031 (17.88); 2.4987 (13.84); 0.5046(16.00); 0.4750 (0.58); 0.3881 (0.95); 0.3519 (1.14); 0.3343 (0.97) 788.7509 (0.61); 8.7433 (1.19); 8.7354 (0.69); 8.1843 (1.79); 7.9746(0.59); 7.9615 (0.62); 7.9492 (1.52); 7.9282 (1.67); 7.9202 (0.72);7.9070 (0.74); 7.7327 (1.06); 7.7128 (0.88); 7.7108 (0.88); 7.6146(3.04); 7.6067 (3.46); 7.5590 (1.25); 7.5546 (0.98); 7.5471 (1.34);7.5395 (0.91); 7.5355 (1.21); 3.3332 (46.14); 2.5340 (0.43); 2.5211(0.97); 2.5117 (7.08); 2.5076 (13.72); 2.5031 (18.01); 2.4986 (13.65);0.5133 (16.00); 0.4148 (0.40); 0.3615 (0.47); 0.3285 (0.32); −0.0002(0.33) 79 8.6813 (0.83); 8.6779 (0.91); 8.6696 (0.89); 8.6662 (0.90);8.1843 (1.77); 7.9687 (0.60); 7.9555 (0.64); 7.9448 (1.76); 7.9245(1.65); 7.9169 (0.74); 7.9035 (0.75); 7.7323 (1.05); 7.7118 (0.89);7.5860 (0.68); 7.5679 (1.12); 7.5544 (1.28); 7.5436 (1.38); 7.5326(1.16); 7.4755 (0.67); 7.4636 (0.67); 7.4559 (0.53); 7.4441 (0.49);6.8931 (0.63); 6.7581 (1.38); 6.6230 (0.69); 3.3342 (49.88); 2.6210(0.36); 2.6101 (0.60); 2.5987 (0.36); 2.5947 (0.36); 2.5250 (0.36);2.5113 (6.65); 2.5073 (13.21); 2.5029 (17.68); 2.4985 (13.56); 0.5173(16.00); 0.3706 (2.27); 0.3533 (1.15) 80 7.9473 (0.57); 7.7084 (0.39);7.6874 (0.51); 7.4970 (0.58); 7.3192 (0.68); 7.3076 (0.47); 7.3003(0.47); 7.2972 (0.50); 3.0952 (16.00); 2.2698 (4.75); 2.2654 (6.28);2.2610 (4.91); 0.2752 (4.73) 81 8.7955 (0.61); 8.7865 (0.84); 8.7801(0.57); 7.9024 (1.00); 7.8908 (1.04); 7.7596 (2.83); 7.7539 (1.47);7.7496 (1.40); 7.4455 (1.06); 7.4373 (1.18); 7.2849 (0.94); 7.2765(0.95); 7.2735 (0.98); 7.2651 (0.82); 5.3016 (0.37); 3.3726 (0.44);3.3545 (0.50); 3.3259 (17.05); 2.5773 (0.35); 2.5635 (0.52); 2.5506(0.36); 2.5242 (0.38); 2.5108 (7.04); 2.5065 (13.77); 2.5020 (18.15);2.4975 (13.50); 2.4933 (6.79); 1.2488 (0.34); 1.2307 (0.73); 0.4679(1.02); 0.4596 (16.00); 0.4212 (0.48); 0.4131 (0.48); 0.3947 (0.60);0.3902 (0.44); 0.2377 (0.53); −0.0002 (2.40) 82 9.0571 (1.17); 9.0514(1.34); 8.9646 (1.32); 8.9588 (1.21); 7.8946 (1.09); 7.8830 (1.13);7.4526 (1.16); 7.4443 (1.27); 7.2744 (0.87); 7.2658 (0.88); 7.2632(0.99); 7.2545 (0.79); 3.3245 (15.84); 3.2779 (1.79); 2.6338 (0.46);2.6204 (0.68); 2.6061 (0.47); 2.5064 (11.35); 2.5021 (15.18); 2.4978(11.81); 0.4543 (16.00); 0.4340 (0.65); 0.4056 (2.75); 0.3913 (3.11);−0.0002 (0.67) 83 8.4530 (0.98); 8.4486 (0.90); 8.4413 (0.85); 8.4366(0.84); 7.8945 (1.10); 7.8830 (1.35); 7.7113 (0.75); 7.7066 (0.79);7.6924 (0.92); 7.6877 (0.91); 7.4956 (0.92); 7.4903 (0.33); 7.4836(0.90); 7.4767 (0.81); 7.4647 (0.75); 7.4434 (1.12); 7.4351 (1.25);7.2772 (0.90); 7.2687 (0.90); 7.2659 (0.97); 7.2574 (0.82); 3.3253(22.38); 3.2274 (2.20); 2.6415 (0.32); 2.6324 (0.61); 2.6212 (0.35);2.5236 (0.34); 2.5062 (12.33); 2.5018 (16.52); 2.4974 (12.70); 0.5014(0.45); 0.4754 (1.06); 0.4674 (16.00); 0.4155 (0.88); 0.3987 (0.76);0.2514 (4.97); −0.0002 (0.57) 84 7.8854 (1.23); 7.8738 (1.31); 7.8643(1.17); 7.8446 (1.19); 7.4369 (1.30); 7.4284 (1.84); 7.4078 (1.15);7.3892 (0.66); 7.2742 (0.93); 7.2629 (1.09); 7.2545 (1.02); 7.1411(0.50); 7.1375 (0.61); 7.1218 (0.85); 7.1185 (0.99); 7.1028 (0.43);7.0991 (0.50); 7.0604 (0.96); 7.0569 (0.93); 7.0414 (0.89); 7.0379(0.82); 3.3336 (65.60); 2.6269 (0.36); 2.6195 (0.41); 2.6105 (0.68);2.6003 (0.46); 2.5925 (0.37); 2.5062 (16.04); 2.5019 (21.16); 2.4977(16.31); 0.4818 (16.00); 0.4459 (1.06); 0.4392 (1.09); 0.4111 (0.46);0.3656 (0.93); 0.2695 (0.80) 85 7.8955 (1.19); 7.8840 (1.23); 7.7905(0.84); 7.7716 (1.01); 7.6937 (0.37); 7.6743 (0.86); 7.6559 (0.63);7.6265 (0.76); 7.6074 (0.88); 7.5884 (0.32); 7.4393 (1.24); 7.4311(1.37); 7.2815 (1.00); 7.2730 (1.04); 7.2704 (1.12); 7.2617 (0.92);7.2505 (0.96); 7.2314 (0.84); 3.3299 (50.14); 2.5690 (0.39); 2.5570(0.63); 2.5423 (0.48); 2.5246 (0.40); 2.5105 (7.76); 2.5064 (15.44);2.5020 (20.69); 2.4976 (15.90); 0.4571 (16.00); 0.3527 (0.46); 0.3049(0.36); 0.2363 (2.20); −0.0002 (0.65) 86 9.0483 (1.06); 9.0426 (1.18);8.9555 (1.18); 8.9498 (1.06); 7.8055 (0.90); 7.8030 (0.97); 7.7992(1.03); 7.7966 (0.95); 7.6496 (0.84); 7.6432 (0.81); 7.6377 (0.93);7.6312 (0.85); 7.3238 (1.05); 7.3215 (1.02); 7.3119 (0.98); 7.3095(0.95); 3.3538 (0.61); 3.3320 (38.19); 3.2766 (1.31); 2.5974 (0.38);2.5832 (0.54); 2.5689 (0.40); 2.5247 (0.42); 2.5112 (7.78); 2.5069(15.10); 2.5024 (19.80); 2.4979 (14.67); 2.4937 (7.33); 1.2309 (0.41);0.4146 (0.84); 0.4109 (1.05); 0.4026 (16.00); 0.3938 (1.36); 0.3866(2.61); 0.3699 (2.02); −0.0002 (0.77) 87 8.7161 (0.71); 8.7123 (0.77);8.7047 (0.78); 8.7008 (0.77); 7.8112 (0.91); 7.8089 (1.01); 7.8050(1.08); 7.8028 (1.01); 7.6578 (0.86); 7.6514 (0.85); 7.6459 (0.98);7.6395 (0.89); 7.6274 (0.46); 7.6102 (1.02); 7.5881 (0.81); 7.5766(0.76); 7.5685 (0.37); 7.5570 (0.35); 7.3144 (1.06); 7.3124 (1.05);7.3025 (1.01); 7.3005 (0.98); 6.9130 (0.62); 6.7780 (1.31); 6.6430(0.66); 3.3259 (24.41); 3.2449 (1.64); 2.6067 (0.40); 2.5927 (0.58);2.5791 (0.39); 2.5240 (0.46); 2.5062 (15.48); 2.5018 (20.24); 2.4974(15.19); 1.2303 (0.46); 0.4161 (16.00); 0.3827 (1.61); 0.3776 (1.60);0.3676 (3.19); −0.0002 (1.76) 88 7.6110 (0.32); 7.4468 (0.44); 3.1531(16.00); 3.0456 (1.22); 2.3214 (3.42); 2.3170 (4.49); 2.3126 (3.41);0.2322 (4.18) 89 7.8520 (1.06); 7.8505 (1.08); 7.8323 (1.12); 7.8308(1.09); 7.7987 (1.08); 7.7962 (1.16); 7.7924 (1.25); 7.7898 (1.17);7.6471 (1.08); 7.6407 (0.99); 7.6352 (1.15); 7.6287 (1.03); 7.4061(0.51); 7.4038 (0.52); 7.3873 (1.09); 7.3851 (1.08); 7.3686 (0.64);7.3663 (0.61); 7.3168 (1.25); 7.3144 (1.25); 7.3049 (1.15); 7.3025(1.14); 7.1256 (0.55); 7.1216 (0.61); 7.1062 (0.88); 7.1024 (0.92);7.0872 (0.50); 7.0832 (0.54); 6.9658 (0.93); 6.9621 (0.93); 6.9468(0.89); 6.9431 (0.83); 3.3523 (0.47); 3.3310 (51.59); 2.9754 (0.40);2.5637 (0.36); 2.5562 (0.42); 2.5470 (0.69); 2.5370 (0.50); 2.5290(0.47); 2.5243 (0.45); 2.5106 (6.97); 2.5063 (13.79); 2.5018 (18.30);2.4973 (13.70); 2.4930 (6.92); 0.4298 (16.00); 0.3466 (0.70); 0.3181(0.74); −0.0002 (0.95) 90 7.8036 (0.89); 7.8011 (0.96); 7.7973 (1.03);7.7947 (0.95); 7.7776 (0.65); 7.7586 (0.79); 7.6687 (0.33); 7.6558(1.01); 7.6496 (1.47); 7.6441 (1.03); 7.6375 (0.96); 7.6334 (0.63);7.6109 (0.55); 7.5918 (0.63); 7.3139 (1.01); 7.3114 (0.99); 7.3020(0.94); 7.2995 (0.92); 7.1336 (0.73); 7.1149 (0.71); 3.3273 (31.39);2.5108 (7.06); 2.5064 (13.82); 2.5018 (18.04); 2.4973 (13.34); 2.4929(6.79); 0.4181 (0.97); 0.4098 (16.00); 0.4015 (0.96); 0.3746 (0.34);0.3047 (0.35); −0.0002 (1.53) 91 8.7785 (0.71); 8.7686 (0.72); 8.7671(0.71); 7.8100 (0.91); 7.8076 (0.98); 7.8037 (1.07); 7.8013 (0.98);7.7478 (0.48); 7.7362 (0.48); 7.7281 (0.74); 7.7164 (0.73); 7.6594(0.93); 7.6530 (1.66); 7.6479 (1.43); 7.6411 (0.92); 7.6330 (0.59);7.3146 (1.05); 7.3123 (1.03); 7.3026 (1.00); 7.3003 (0.97); 3.3266(22.37); 2.5242 (0.61); 2.5198 (0.71); 2.5108 (6.10); 2.5066 (11.40);2.5021 (14.95); 2.4976 (11.44); 0.4202 (1.04); 0.4120 (16.00); −0.0002(0.55) 92 8.6639 (0.51); 8.6608 (0.55); 8.6522 (0.55); 8.6490 (0.55);7.9089 (0.48); 7.8897 (0.54); 7.5649 (0.38); 7.5530 (0.39); 7.5453(0.37); 7.5335 (0.34); 7.1762 (0.54); 7.1567 (1.09); 7.1382 (0.86);7.0162 (1.53); 6.9969 (1.40); 6.9878 (0.57); 6.8521 (0.92); 6.7167(0.46); 3.2520 (32.41); 2.9720 (1.32); 2.6631 (0.41); 2.4348 (6.06);2.4306 (12.01); 2.4261 (16.00); 2.4217 (12.18); 2.1647 (2.80); 0.3668(0.66); 0.3493 (0.68); 0.3028 (0.77); 0.2941 (0.63); −0.0002 (11.18);−0.0758 (1.12) 93 8.9785 (0.79); 8.9729 (0.90); 8.8808 (0.88); 8.8753(0.81); 7.1739 (0.60); 7.1546 (1.11); 7.1359 (1.01); 7.0097 (1.99);6.9920 (1.59); 3.2924 (0.35); 3.2551 (37.41); 2.9967 (0.83); 2.5962(0.35); 2.5858 (0.50); 2.4447 (0.35); 2.4313 (6.07); 2.4271 (12.00);2.4226 (16.00); 2.4182 (12.16); 2.1621 (2.96); 1.1509 (0.46); 0.3809(0.64); 0.3636 (0.69); 0.3168 (0.60); 0.0081 (1.04); −0.0002 (12.13);−0.0801 (0.76) 94 8.3822 (0.60); 8.3775 (0.64); 8.3702 (0.65); 8.3655(0.64); 7.8039 (0.58); 7.7992 (0.62); 7.7850 (0.68); 7.7802 (0.66);7.4365 (0.66); 7.4244 (0.66); 7.4175 (0.62); 7.4055 (0.59); 7.1700(0.56); 7.1492 (1.04); 7.1317 (0.93); 7.0073 (1.98); 6.9890 (1.59);3.2453 (16.00); 2.9167 (0.42); 2.6490 (0.34); 2.6348 (0.45); 2.6201(0.33); 2.4301 (4.44); 2.4258 (8.88); 2.4213 (11.86); 2.4168 (8.96);2.4125 (4.59); 2.1605 (2.81); 0.3729 (1.23); 0.3571 (1.28); 0.0076(0.60); −0.0002 (11.49); −0.0806 (1.24) 95 7.7779 (0.49); 7.7598 (0.51);7.7581 (0.51); 7.3459 (0.52); 7.3436 (0.52); 7.3272 (0.33); 7.3248(0.32); 7.1549 (0.83); 7.1510 (0.66); 7.1358 (1.24); 7.1170 (0.67);7.0359 (0.43); 7.0320 (0.43); 7.0029 (0.95); 6.9853 (0.73); 6.9721(0.45); 3.2308 (16.00); 2.5785 (0.35); 2.4167 (4.72); 2.4123 (9.31);2.4077 (12.30); 2.4032 (9.14); 2.3989 (4.57); 2.1587 (2.05); 0.3340(0.55); 0.3141 (0.34); −0.0002 (8.48); −0.0080 (0.47); −0.0937 (1.18) 967.7283 (0.61); 7.7088 (0.76); 7.6457 (0.65); 7.6270 (0.45); 7.5677(0.43); 7.5484 (0.60); 7.4298 (0.70); 7.4108 (0.59); 7.1817 (0.66);7.1615 (1.20); 7.1488 (0.32); 7.1434 (1.04); 7.0186 (2.10); 7.0000(1.81); 3.2546 (18.43); 2.5569 (0.46); 2.4535 (0.33); 2.4401 (6.12);2.4357 (12.10); 2.4311 (16.00); 2.4266 (11.90); 2.4223 (5.97); 2.1611(3.20); 0.0077 (0.72); −0.0002 (13.48); −0.0080 (0.75); −0.0707 (2.15)97 8.7304 (0.78); 8.7191 (0.81); 7.9694 (0.74); 7.9499 (0.85); 7.7227(0.69); 7.7110 (0.69); 7.7030 (0.63); 7.6912 (0.59); 7.1824 (0.86);7.1618 (1.57); 7.1499 (0.36); 7.1441 (1.36); 7.0186 (2.98); 7.0003(2.45); 6.9816 (0.38); 3.2539 (18.23); 2.5819 (0.34); 2.5684 (0.55);2.5577 (0.35); 2.4528 (0.32); 2.4351 (12.08); 2.4306 (16.00); 2.4262(12.17); 2.1605 (4.17); 0.3828 (0.48); −0.0002 (16.50); −0.0714 (0.81)98 8.7397 (2.95); 8.7309 (2.92); 8.7279 (2.96); 7.9930 (2.64); 7.9737(2.94); 7.6455 (2.02); 7.6336 (2.07); 7.6260 (1.97); 7.6140 (1.82);7.4001 (3.07); 7.3799 (3.42); 7.2731 (0.84); 7.2679 (1.30); 7.2541(4.25); 7.2487 (6.63); 7.2297 (3.19); 7.2129 (1.03); 7.2103 (1.03);7.1371 (1.71); 7.1316 (1.60); 7.1168 (2.14); 7.1002 (1.22); 7.0947(1.16); 7.0668 (2.27); 6.9315 (4.74); 6.7962 (2.41); 3.3521 (0.47);3.3276 (92.93); 3.1005 (7.59); 2.8902 (0.38); 2.7799 (0.52); 2.7697(1.12); 2.7621 (1.42); 2.7518 (2.15); 2.7427 (1.32); 2.7357 (1.17);2.7256 (0.61); 2.6706 (0.44); 2.6663 (0.41); 2.5065 (43.07); 2.5021(57.71); 2.4977 (44.59); 2.4196 (16.00); 2.3290 (0.39); 1.2347 (0.60);0.4748 (0.62); 0.4571 (3.43); 0.4406 (3.66); 0.4295 (2.13); 0.4109(1.84); 0.4007 (4.53); 0.3720 (0.70); 0.1072 (55.93); 0.0752 (1.28);−0.0002 (1.42) 99 8.9484 (0.76); 8.9426 (0.87); 8.8526 (0.87); 8.8468(0.81); 7.2913 (0.58); 7.2720 (0.66); 7.2700 (0.66); 7.1422 (0.90);7.1368 (1.34); 7.1226 (0.68); 7.1200 (0.66); 7.0291 (0.36); 7.0122(0.33); 7.0089 (0.41); 7.0039 (0.35); 3.2158 (11.59); 3.0275 (0.75);2.5730 (0.42); 2.4136 (0.35); 2.4002 (6.07); 2.3958 (12.05); 2.3913(16.00); 2.3867 (11.90); 2.3824 (5.94); 2.3176 (3.11); 1.1200 (0.40);0.3665 (0.59); 0.3497 (0.65); 0.3116 (0.60); 0.0250 (0.85); 0.0077(0.93); −0.0002 (11.61); −0.1113 (1.99) 100 8.3536 (0.71); 8.3489(0.76); 8.3416 (0.77); 8.3370 (0.76); 7.7787 (0.71); 7.7740 (0.74);7.7598 (0.82); 7.7550 (0.80); 7.4088 (0.80); 7.3969 (0.79); 7.3900(0.76); 7.3779 (0.73); 7.2869 (0.70); 7.2675 (0.77); 7.1404 (1.01);7.1351 (1.54); 7.1189 (0.75); 7.1164 (0.73); 7.0249 (0.40); 7.0192(0.37); 7.0047 (0.50); 3.2128 (16.00); 2.6340 (0.37); 2.6191 (0.52);2.6050 (0.38); 2.3945 (10.35); 2.3900 (13.72); 2.3856 (10.35); 2.3131(3.72); 0.3590 (1.57); 0.3434 (1.39); 0.1395 (0.56); −0.0002 (12.50);−0.1123 (1.33) 101 7.0088 (0.32); 3.2130 (16.00); 2.3862 (1.60); 2.3822(3.14); 2.3777 (4.17); 2.3732 (3.15); 2.3081 (0.98); −0.0002 (3.80) 1027.1452 (0.45); 3.2342 (16.00); 2.4101 (1.79); 2.4058 (3.54); 2.4013(4.71); 2.3967 (3.53); 2.3925 (1.78); 2.3124 (0.98); −0.0002 (3.77);−0.1016 (0.33) 103 8.8048 (2.82); 8.7941 (2.90); 8.0489 (2.63); 8.0303(3.05); 7.7992 (2.46); 7.7875 (2.47); 7.7795 (2.28); 7.7677 (2.21);7.4011 (3.18); 7.3807 (3.45); 7.2721 (0.64); 7.2660 (1.18); 7.2516(5.09); 7.2471 (7.09); 7.2330 (3.26); 7.2308 (3.22); 7.2139 (1.06);7.2119 (1.00); 7.1385 (1.76); 7.1324 (1.58); 7.1180 (2.14); 7.1018(1.26); 7.0962 (1.15); 3.3258 (80.24); 3.1654 (0.36); 3.0298 (0.33);3.0154 (0.38); 3.0049 (0.37); 2.9968 (0.40); 2.9787 (0.37); 2.8909(0.53); 2.7317 (0.41); 2.6818 (0.65); 2.6673 (1.56); 2.6541 (1.98);2.6427 (1.24); 2.6274 (0.73); 2.5245 (1.17); 2.5108 (23.53); 2.5067(46.77); 2.5023 (62.54); 2.4979 (48.00); 2.4132 (16.00); 2.3291 (0.42);2.3246 (0.32); 2.2113 (0.60); 1.2352 (0.63); 0.4675 (1.78); 0.2513(0.41); 0.1322 (0.60); 0.1028 (57.38); 0.0705 (0.69); −0.0002 (2.71) 1048.7424 (3.05); 8.7394 (3.27); 8.7307 (3.32); 8.7276 (3.27); 8.0009(2.93); 7.9814 (3.26); 7.6440 (2.28); 7.6321 (2.34); 7.6244 (2.22);7.6125 (2.07); 7.2822 (2.33); 7.2627 (5.59); 7.2432 (3.74); 7.1695(5.42); 7.1411 (3.12); 7.1213 (2.22); 7.0673 (5.14); 7.0456 (2.91);6.9325 (5.48); 6.7972 (2.81); 3.3299 (134.57); 3.0429 (8.14); 2.8906(0.47); 2.7795 (0.58); 2.7692 (1.25); 2.7616 (1.61); 2.7514 (2.45);2.7423 (1.49); 2.7348 (1.36); 2.7250 (0.68); 2.6716 (0.40); 2.5247(1.24); 2.5069 (44.91); 2.5024 (59.35); 2.4980 (44.63); 2.3290 (0.40);2.3248 (0.33); 2.2823 (16.00); 1.2350 (0.62); 0.4504 (3.97); 0.4330(4.03); 0.4214 (1.78); 0.3958 (1.86); 0.3860 (4.59); 0.3773 (3.76);0.3580 (0.82); 0.2313 (0.37); 0.0831 (63.20); 0.0374 (0.76); −0.0002(1.41); −0.0684 (0.36) 105 8.9702 (0.78); 8.9644 (0.89); 8.8750 (0.89);8.8692 (0.84); 7.1937 (0.41); 7.1742 (0.97); 7.1548 (0.68); 7.0758(0.92); 7.0533 (0.59); 7.0338 (0.45); 6.9724 (0.60); 6.9532 (0.49);3.2364 (11.24); 2.9803 (0.88); 2.5792 (0.48); 2.4345 (0.34); 2.4208(6.17); 2.4167 (12.08); 2.4123 (16.00); 2.4078 (12.04); 2.4038 (6.17);2.1931 (2.74); 1.1410 (0.39); 0.3772 (0.64); 0.3598 (0.69); 0.3122(0.60); 0.0369 (0.41); 0.0073 (1.18); −0.0002 (11.19); −0.0902 (2.03);−0.1390 (0.60) 106 7.1720 (0.37); 7.0785 (0.33); 3.2471 (16.00); 2.4226(1.75); 2.4182 (3.48); 2.4137 (4.63); 2.4091 (3.45); 2.4047 (1.72);2.1924 (0.99); 0.3719 (0.46); 0.3563 (0.51); −0.0002 (4.26); −0.0068(0.42) 107 7.7737 (0.43); 7.7720 (0.44); 7.7540 (0.47); 7.7523 (0.45);7.3404 (0.46); 7.3382 (0.46); 7.1572 (1.01); 7.1379 (0.76); 7.0756(0.58); 7.0715 (0.42); 7.0318 (0.67); 7.0126 (0.48); 7.0092 (0.41);6.9701 (0.38); 3.2250 (16.00); 2.4094 (3.46); 2.4051 (6.82); 2.4006(9.04); 2.3961 (6.75); 2.3918 (3.40); 2.1941 (1.66); 0.3332 (0.49);−0.0002 (7.13); −0.1013 (0.80); −0.1505 (0.38) 108 7.7240 (0.52); 7.7045(0.62); 7.6412 (0.56); 7.6223 (0.38); 7.5642 (0.40); 7.5450 (0.52);7.4391 (0.56); 7.4200 (0.47); 7.2044 (0.39); 7.1849 (0.84); 7.1655(0.61); 7.0890 (0.81); 7.0621 (0.51); 7.0421 (0.41); 6.9841 (0.54);6.9652 (0.46); 3.2672 (0.81); 3.2471 (16.00); 2.5625 (0.40); 2.4331(6.04); 2.4288 (10.57); 2.4244 (13.54); 2.4200 (10.31); 2.1957 (2.27);0.0498 (0.33); 0.0190 (0.60); −0.0002 (9.69); −0.0779 (1.40); −0.1266(0.63) 109 8.8050 (3.17); 8.7942 (3.27); 8.0599 (2.96); 8.0406 (3.41);7.7981 (2.73); 7.7864 (2.75); 7.7784 (2.54); 7.7667 (2.39); 7.2837(2.35); 7.2642 (5.58); 7.2448 (3.71); 7.1677 (5.43); 7.1428 (3.15);7.1231 (2.21); 7.0617 (3.50); 7.0426 (2.92); 3.3263 (85.63); 3.1233(0.40); 3.1174 (0.40); 3.0149 (0.34); 2.9975 (0.34); 2.9784 (0.34);2.9610 (0.35); 2.9235 (0.40); 2.8909 (0.79); 2.7317 (0.48); 2.6804(0.74); 2.6672 (1.66); 2.6528 (2.20); 2.6424 (1.39); 2.6262 (0.66);2.5067 (50.80); 2.5024 (67.08); 2.4981 (51.47); 2.3335 (0.33); 2.3292(0.46); 2.2732 (16.00); 2.1024 (0.53); 1.2351 (0.72); 0.4590 (1.94);0.3612 (0.54); 0.3328 (0.49); 0.2268 (0.43); 0.0785 (62.96); 0.0520(0.61); −0.0003 (2.57); −0.0728 (0.34) 110 8.7411 (3.09); 8.7321 (3.07);8.7294 (3.11); 7.9985 (2.81); 7.9791 (3.11); 7.6464 (2.15); 7.6346(2.20); 7.6269 (2.09); 7.6151 (1.93); 7.5437 (4.80); 7.5388 (5.22);7.3397 (1.39); 7.3348 (1.21); 7.3188 (4.75); 7.3138 (5.10); 7.3024(7.93); 7.2816 (2.11); 7.0671 (2.30); 6.9318 (4.95); 6.7965 (2.52);3.3306 (161.79); 3.0911 (8.18); 2.8912 (0.45); 2.7902 (0.54); 2.7801(1.15); 2.7723 (1.46); 2.7621 (2.26); 2.7531 (1.42); 2.7462 (1.21);2.7357 (0.63); 2.6718 (0.48); 2.6675 (0.37); 2.5248 (1.35); 2.5071(51.24); 2.5027 (68.35); 2.4984 (52.85); 2.4200 (16.00); 2.3338 (0.35);2.3294 (0.45); 2.3251 (0.36); 1.2350 (0.66); 0.4823 (0.65); 0.4653(3.60); 0.4488 (3.83); 0.4378 (2.27); 0.4197 (1.98); 0.4095 (4.78);0.3808 (0.71); 0.2556 (0.34); 0.1072 (57.78); −0.0002 (1.44) 111 8.9479(0.33); 8.9421 (0.38); 8.8535 (0.38); 8.8478 (0.36); 7.4332 (0.39);7.4282 (0.41); 7.2079 (0.40); 7.2028 (0.42); 7.1898 (0.62); 3.2215(16.00); 3.0215 (0.33); 2.3995 (3.00); 2.3953 (5.80); 2.3908 (7.58);2.3863 (5.62); 2.3821 (2.82); 2.3159 (1.24); −0.0002 (4.79); −0.1124(0.84) 112 8.3552 (0.33); 8.3505 (0.36); 8.3432 (0.36); 8.3385 (0.36);7.7780 (0.33); 7.7638 (0.36); 7.7590 (0.35); 7.4299 (0.46); 7.4249(0.49); 7.4101 (0.39); 7.3981 (0.37); 7.3912 (0.36); 7.3791 (0.34);7.2060 (0.49); 7.2009 (0.52); 7.1898 (0.78); 3.2163 (16.00); 2.3992(2.99); 2.3949 (5.93); 2.3904 (7.89); 2.3858 (5.91); 2.3815 (2.99);2.3132 (1.53); 0.3673 (0.69); 0.3515 (0.59); 0.1394 (0.40); −0.0002(5.58); −0.1124 (0.58) 113 7.7521 (0.91); 7.7324 (0.98); 7.4109 (1.16);7.3386 (0.42); 7.3367 (0.40); 7.3198 (0.94); 7.3012 (0.58); 7.1901(3.39); 7.1356 (0.78); 7.1319 (0.89); 7.1166 (0.70); 7.1129 (0.71);7.0303 (0.54); 7.0263 (0.51); 7.0109 (0.81); 7.0074 (0.77); 6.9919(0.47); 6.9880 (0.43); 3.1997 (15.48); 2.5817 (0.33); 2.5730 (0.59);2.5619 (0.36); 2.5548 (0.33); 2.4001 (0.33); 2.3866 (6.28); 2.3824(12.16); 2.3780 (16.00); 2.3735 (11.97); 2.3114 (3.53); 0.3373 (0.97);0.2950 (0.60); 0.1460 (0.58); 0.0443 (0.51); −0.0002 (13.57); −0.0092(1.12); −0.0503 (0.41); −0.1243 (1.90) 114 7.7026 (0.44); 7.6830 (0.56);7.6203 (0.48); 7.6018 (0.33); 7.5427 (0.33); 7.5236 (0.45); 7.4408(0.70); 7.4359 (0.75); 7.4140 (0.49); 7.3949 (0.41); 7.2169 (0.73);7.2118 (0.77); 7.1997 (1.18); 7.1789 (0.33); 3.2244 (16.00); 2.5539(0.32); 2.4098 (5.08); 2.4057 (9.91); 2.4012 (13.06); 2.3968 (9.87);2.3928 (5.07); 2.3128 (2.06); 0.1356 (0.36); 0.0364 (0.37); 0.0091(0.69); −0.0002 (8.37); −0.1011 (1.58) 115 8.8068 (2.97); 8.7960 (3.02);8.0557 (2.76); 8.0364 (3.16); 7.8006 (2.60); 7.7888 (2.61); 7.7809(2.38); 7.7691 (2.34); 7.5439 (5.16); 7.5388 (5.48); 7.4341 (0.57);7.4292 (0.55); 7.3409 (1.62); 7.3358 (1.42); 7.3313 (0.48); 7.3201(4.98); 7.3149 (5.16); 7.3004 (8.13); 7.2795 (2.55); 3.3257 (76.96);3.1640 (0.38); 3.1598 (0.38); 3.1540 (0.38); 3.0337 (0.34); 3.0162(0.38); 2.9978 (0.41); 2.9782 (0.39); 2.8914 (0.58); 2.7320 (0.43);2.6917 (0.63); 2.6765 (1.62); 2.6721 (1.44); 2.6638 (2.24); 2.6528(1.32); 2.6370 (0.64); 2.5245 (1.31); 2.5113 (25.17); 2.5072 (49.69);2.5027 (66.08); 2.4983 (50.20); 2.4134 (16.00); 2.3338 (0.32); 2.3295(0.44); 2.3249 (0.34); 2.2097 (0.62); 1.2349 (0.71); 0.4763 (1.83);0.4414 (1.28); 0.3730 (0.61); 0.3644 (3.43); 0.3281 (0.48); 0.2514(0.41); 0.1470 (0.60); 0.1027 (60.58); 0.0590 (0.71); 0.0254 (0.32);−0.0002 (3.17); −0.0491 (0.33) 116 8.9599 (0.36); 8.9537 (0.52); 8.9467(0.36); 8.8666 (0.44); 8.8619 (0.69); 7.1933 (0.41); 7.0782 (0.91);7.0736 (0.84); 5.2039 (0.67); 3.2729 (0.70); 3.2547 (0.82); 3.2279(16.00); 2.9618 (0.54); 2.9438 (0.33); 2.4239 (0.37); 2.4105 (6.12);2.4062 (11.92); 2.4017 (15.68); 2.3971 (11.68); 2.3929 (5.88); 2.2202(1.09); 1.1485 (0.59); 1.1305 (1.25); 1.1123 (0.56); 0.3696 (0.71);0.1474 (2.24); 0.1423 (1.77); 0.1355 (1.21); 0.1305 (0.53); 0.0059(1.24); −0.0002 (5.70); −0.0074 (0.89); −0.0109 (0.76); −0.1010 (2.11)117 8.6524 (0.46); 8.6503 (0.46); 8.6411 (0.49); 7.9232 (0.36); 7.9037(0.40); 7.5555 (0.33); 7.5436 (0.34); 7.5360 (0.32); 7.1996 (0.64);7.1954 (0.40); 7.0888 (1.46); 7.0845 (1.40); 6.8439 (0.61); 5.2135(0.65); 3.2822 (0.68); 3.2640 (0.73); 3.2356 (16.00); 2.9484 (1.04);2.6710 (0.42); 2.4151 (10.48); 2.4109 (13.58); 2.4067 (10.42); 2.2287(1.79); 1.1578 (0.63); 1.1398 (1.31); 1.1216 (0.59); 0.3652 (0.64);0.3486 (0.59); 0.3026 (0.59); 0.2942 (0.49); 0.1569 (0.39); 0.1552(0.39); 0.1518 (0.41); 0.0091 (0.85); −0.0002 (7.33); −0.0078 (0.97);−0.0916 (1.59) 118 8.3693 (0.66); 8.3647 (0.71); 8.3574 (0.72); 8.3527(0.71); 7.8119 (0.63); 7.8072 (0.65); 7.7930 (0.74); 7.7882 (0.70);7.4244 (0.71); 7.4124 (0.70); 7.4055 (0.68); 7.3935 (0.65); 7.1971(0.53); 7.1925 (1.03); 7.1879 (0.61); 7.0830 (2.34); 7.0784 (2.20);5.2039 (0.45); 3.2743 (0.44); 3.2561 (0.48); 3.2268 (16.00); 2.6458(0.35); 2.6323 (0.52); 2.6179 (0.35); 2.4081 (11.24); 2.4037 (14.64);2.3992 (10.95); 2.2203 (2.69); 1.1504 (0.40); 1.1323 (0.87); 1.1141(0.38); 0.3687 (1.46); 0.3536 (1.62); −0.0002 (11.45); −0.0088 (1.05);−0.0988 (1.96) 119 7.7669 (0.78); 7.7650 (0.80); 7.7471 (0.84); 7.7452(0.81); 7.3530 (0.36); 7.3504 (0.37); 7.3342 (0.80); 7.3317 (0.80);7.3154 (0.50); 7.3129 (0.49); 7.1802 (0.58); 7.1755 (1.15); 7.1708(0.71); 7.1641 (0.73); 7.1602 (0.77); 7.1450 (0.62); 7.1412 (0.60);7.0818 (2.55); 7.0771 (2.36); 7.0457 (0.43); 7.0417 (0.42); 7.0264(0.68); 7.0227 (0.65); 7.0074 (0.42); 7.0033 (0.38); 5.1926 (0.52);3.2627 (0.49); 3.2445 (0.52); 3.2147 (15.88); 2.5837 (0.47); 2.5663(0.33); 2.4149 (0.35); 2.4014 (6.13); 2.3970 (12.11); 2.3924 (16.00);2.3879 (11.83); 2.3834 (5.82); 2.2253 (2.69); 1.1389 (0.44); 1.1208(0.95); 1.1027 (0.42); 0.3333 (0.84); 0.3155 (0.60); 0.2997 (0.54);0.0076 (0.78); −0.0002 (12.69); −0.0083 (1.25); −0.1097 (2.59) 1207.7187 (0.61); 7.6991 (0.76); 7.6360 (0.66); 7.6174 (0.47); 7.5598(0.44); 7.5407 (0.61); 7.4446 (0.67); 7.4257 (0.58); 7.2078 (0.54);7.2032 (1.05); 7.1986 (0.62); 7.0924 (2.39); 7.0878 (2.26); 5.2155(0.55); 3.2872 (0.68); 3.2689 (1.12); 3.2509 (53.88); 2.5818 (0.37);2.5666 (0.45); 2.4396 (0.36); 2.4260 (6.35); 2.4218 (12.24); 2.4173(16.00); 2.4128 (11.91); 2.2258 (2.78); 1.1635 (0.48); 1.1455 (1.04);1.1273 (0.46); −0.0002 (11.90); −0.0080 (1.19); −0.0859 (1.64) 1218.8079 (3.31); 8.7965 (3.35); 8.0747 (3.08); 8.0551 (3.49); 7.8021(2.92); 7.7903 (2.93); 7.7823 (2.76); 7.7706 (2.54); 7.2973 (3.09);7.2927 (6.17); 7.2881 (3.71); 7.1794 (13.76); 7.1748 (13.14); 6.8966(0.43); 6.8921 (0.43); 3.3285 (138.88); 3.1080 (0.42); 3.0805 (0.40);3.0452 (0.36); 3.0332 (0.34); 3.0159 (0.37); 2.9970 (0.37); 2.9740(0.37); 2.9356 (0.42); 2.8915 (0.83); 2.7323 (0.50); 2.6924 (0.66);2.6768 (1.70); 2.6722 (1.58); 2.6646 (2.42); 2.6541 (1.44); 2.6377(0.71); 2.5252 (1.37); 2.5118 (26.36); 2.5075 (52.59); 2.5029 (70.23);2.4985 (53.31); 2.4943 (27.71); 2.3296 (0.65); 2.3110 (16.00); 2.1415(0.52); 1.2349 (0.80); 0.4668 (2.02); 0.3766 (0.56); 0.3434 (0.49);0.3329 (0.47); 0.2357 (0.44); 0.0873 (66.37); −0.0002 (2.95); −0.0642(0.38)

Intensity of sharp signals correlates with the height of the signals ina printed example of a NMR spectrum in cm and shows the real relationsof signal intensities. From broad signals several peaks or the middle ofthe signal and their relative intensity in comparison to the mostintensive signal in the spectrum can be shown.

The ¹H-NMR peak lists are similar to classical ¹H-NMR prints and containtherefore usually all peaks, which are listed at classicalNMR-interpretation. Additionally they can show like classical ¹H-NMRprints signals of solvents, stereoisomers of the target compounds, whichare also object of the invention, and/or peaks of impurities. To showcompound signals in the delta-range of solvents and/or water the usualpeaks of solvents, for example peaks of DMSO in DMSO-d6 and the peak ofwater are shown in our ¹H-NMR peak lists and have usually on average ahigh intensity.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities have usually on average a lower intensity than the peaks oftarget compounds (for example with a purity >90%). Such stereoisomersand/or impurities can be typical for the specific preparation process.Therefore their peaks can help to recognize the reproduction of ourpreparation process via “side-products-fingerprints”.

An expert, who calculates the peaks of the target compounds with knownmethods (MestreC, ACD-simulation, but also with empirically evaluatedexpectation values), can isolate the peaks of the target compounds asneeded optionally using additional intensity filters. This isolationwould be similar to relevant peak picking at classical ¹H-NMRinterpretation.

Further details of NMR-data description with peak lists can be found inthe publication “Citation of NMR Peaklist Data within PatentApplications” of the Research Disclosure Database Number 564025.

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

GENERAL PREPARATION EXAMPLE 1 Preparation of Amide of Formula (I) onChemspeed™ Apparatus

In a 13 mL Chemspeed™ vial is distributed 4 mL of a 0.15 molar solutionof the amine (II) (0.60 mmol) in dichloromethane followed by 0.72 mmolof triethylamine. At a rate of 1 mL/mn, 2 mL of a 0.30 molar solution ofthe acyl chloride (III) (L¹=Cl) (0.60 mmole) are added and the mixtureis then stirred at room temperature overnight. 1 mL of water is thenadded and the mixture is poured over a basic alumina cartridge (2 g) andeluted with dichloromethane. The solvents are removed and the crudeamide derivative is analyzed by LCMS and NMR. Insufficiently purecompounds are further purified by preparative LCMS.

GENERAL PREPARATION EXAMPLE 2 Thionation of Amide of Formula (I) onChemspeed™ Apparatus

In a 13 mL Chemspeed™ vial is weighted 0.27 mmol of phosphorouspentasulfide (P₂S₅). 3 mL of a 0.18 molar solution of the amide (I)(0.54 mmol) in dioxane is added and the mixture is heated at reflux fortwo hours. The temperature is then cooled to 80° C. and 2.5 mL of waterare added. The mixture is heated at 80° C. for one more hour. 2 mL ofwater are then added and the reaction mixture is extracted twice by 4 mLof dichloromethane. The organic phase is deposited on a basic aluminacartridge (2 g) and eluted twice by 8 mL of dichloromethane. Thesolvents are removed and the crude thioamide derivative is analyzed byLCMS and NMR. Insufficiently pure compounds are further purified bypreparative LCMS.

PREPARATION EXAMPLE 3

Preparation of2-(difluoromethyl)-N-{[dimethyl(phenyl)silyl]methyl}nicotinamide(compound 1) 121 mg (0.6 mmol) of 1-[dimethyl(phenyl)silyl]methanamineare reacted with 126 mg (0.66 mmol) of 2-(difluoromethyl)nicotinoylchloride according to the general preparation example 1, to yield 142 mg(72%) 2-(difluoromethyl)-N-{[dimethyl(phenyl)silyl]methyl}nicotinamideof 97% purety. (M+H=321).

EXAMPLE A In Vivo Preventive Test on Sphaerotheca fuliginea (PowderyMildew on Cucurbits)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO and then diluted with water to obtain thedesired active material concentration.

Gherkin plants (“Vert petit de Paris” variety), sown in starter cups ona 50/50 peat soil-pozzolana substrate and grown at 24° C., are treatedat the Z11 cotyledon stage by spraying with the active ingredientprepared as described above. Plants, used as controls, are treated withthe mixture of acetone/tween/DMSO/water not containing the activematerial.

After 24 hours, the plants are contaminated by spraying the cotyledonswith an aqueous suspension of Sphaerotheca fuliginea spores (100 000spores per mL). The spores are collected from infected plants. Thecontaminated gherkin plants are incubated at about 20° C. and at 70-80%relative humidity.

Grading (% of efficacy) is carried out 12 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) to excellent (at least 95%)protection is observed at a dose of 500 ppm of active ingredient withthe following compounds from table A:

TABLE A Example Efficacy 1 98 2 83 5 89 10 78 11 94 14 98 15 72 20 10021 98 22 78 26 93 36 94 41 78 44 94 45 83 48 98 50 98 52 94 54 83 56 8362 79 63 71

EXAMPLE B In Vivo Preventive Test on Alternaria solani (Tomato)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Alternaria solani. The plants remain for one day inan incubation cabinet at approximately 22° C. and a relative atmospherichumidity of 100%. Then the plants are placed in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 96%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control while an efficacy of100% means that no disease is observed.

Under these conditions, good (at least 90%) to excellent (at least 95%)protection is observed at a dose of 500 ppm of active ingredient withthe following compounds from table B:

TABLE B Example Efficacy 1 95 28 89 29 95 32 89 34 89 62 94 63 95 72 8974 78 77 78 79 89 86 75 87 88 91 78 92 78 93 75 104 90 110 70 117 75

EXAMPLE C In Vivo Preventive Test on Pyrenophora teres (Barley)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Pyrenophora teres. The plants remain for 48 hours inan incubation cabinet at 22° C. and a relative atmospheric humidity of100%. Then the plants are placed in a greenhouse at a temperature ofapproximately 20° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 7-9 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table C:

TABLE C Example Efficacy 1 90 7 100 8 100 9 100 10 100 11 97 12 97 13100 14 100 15 100 16 100 17 86 20 100 21 100 26 95 28 100 29 95 32 95 3380 34 100 44 93 47 97 48 97 49 97 50 97 51 97 52 100 54 100 55 97 56 10058 100 62 100 63 95 68 80 72 95 74 95 77 100 78 95 79 95 82 95 86 90 87100 91 70 92 90 93 70 99 70 104 80 105 70 110 95 111 95 117 90

EXAMPLE D In Vivo Preventive Test on Pyrenophora teres (Barley)—2nd Test

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Barley plants (“Plaisant” variety), sown in starter cups on a 50/50 peatsoil pozzolana substrate and grown at 22° C., are treated at the 1 leafstage (10 cm height) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Pyrenophora teres spores (12 000 spores permL). The spores are collected from a 12-day-old culture. Thecontaminated barley plants are incubated for 48 hours at 20° C. and at100% relative humidity, and then for 12 days at 20° C. at 70-80%relative humidity.

Grading (% of efficacy) is carried out 14 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) to excellent (at least 90%)protection is observed at a dose of 500 ppm of active ingredient withthe following compounds from table D:

TABLE D Example Efficacy 1 79 42 93 62 93

EXAMPLE E In Vivo Preventive Test on Septoria tritici (Wheat)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Wheat plants (“Scipion” variety), sown in starter cups on a 50/50 peatsoil pozzolana substrate and grown at 22° C., are treated at the 1 leafstage (10 cm height) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of cryopreserved Septoria tritici spores (500 000spores per mL). The contaminated wheat plants are incubated for 72 hoursat 18° C. and at 100% relative humidity, and then for 21 days at 90%relative humidity.

Grading (% of efficacy) is carried out 24 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table E:

TABLE E Example Efficacy 1 100 2 100 3 90 5 80 7 93 8 100 9 86 10 79 1279 13 97 14 93 15 71 16 71 17 79 20 93 21 86 22 96 26 100 36 90 38 80 3996 40 96 41 90 42 100 44 86 45 80 47 93 48 93 49 100 51 100 52 97 54 9355 64 56 100 62 100 63 96

EXAMPLE F In Vivo Preventive Test on Puccinia recondita (Brown Rust onWheat)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Wheat plants (“Scipion” variety), sown in starter cups on a 50/50 peatsoil pozzolana substrate and grown at 22° C., are treated at the 1 leafstage (10 cm height) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Puccinia recondita spores (100 000 spores permL). The spores are collected from an infected plant and are suspendedin water containing 2.5 mL/L of Tween 80 at 10%. The contaminated wheatplants are incubated for 24 hours at 20° C. and at 100% relativehumidity, and then for 10 days at 20° C. and at 70-80% relativehumidity.

Grading (% of efficacy) is carried out 12 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table F:

TABLE F Example Efficacy 1 88 2 88 3 75 11 88 14 98 15 75 20 88 21 75 22100 26 92 36 81 42 72 44 75 45 75 48 88 49 88 50 75 51 88 62 92 63 97

EXAMPLE G In Vivo Preventive Test on Alternaria brassicae (Leaf Spot onRadish)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Radish plants (“Pernod Clair” variety), sown in starter cups on a 50/50peat soil pozzolana substrate and grown at 17° C., are treated at thecotyledon stage by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying the cotyledonswith an aqueous suspension of Alternaria brassicae spores (50 000 sporesper mL). The spores are collected from a 15-day-old culture. Thecontaminated radish plants are incubated at 20° C. and at 100% relativehumidity.

Grading (% of efficacy) is carried out 6 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 75%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table G:

TABLE G Example Efficacy 5 96 8 88 10 88 11 88 12 88 14 95 16 95 20 7536 90 44 75 45 90 47 75 48 75 49 75 50 75 52 100 56 88

EXAMPLE H In Vivo Preventive Test on Botrytis cinerea (Cucumber)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Botrytis cinerea. The plants remain for two days inan incubation cabinet at approximately 22° C. and a relative atmospherichumidity of 100%. Then the plants are placed in an incubation cabinet atapproximately 14° C. and a relative atmospheric humidity of 96%.

The test is evaluated 5-6 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table H:

TABLE H Example Efficacy 26 99 32 94 34 85 77 95 79 70 86 80 92 98 93100 105 93

EXAMPLE I In Vivo Preventive Test on Botrytis cinerea (Grey Mould)—2ndTest

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO and then diluted with water to obtain thedesired active material concentration.

Gherkin plants (“Vert petit de Paris” variety), sown in starter cups ona 50/50 peat soil pozzolana substrate and grown at 24° C., are treatedat the Z11 cotyledon stage by spraying with the active ingredientprepared as described above. Plants, used as controls, are treated withthe mixture of acetone/tween/DMSO/water not containing the activematerial.

After 24 hours, the plants are contaminated by spraying the cotyledonswith an aqueous suspension of cryopreserved Botrytis cinerea spores (50000 spores per mL). The spores are suspended in a nutrient solutioncomposed of 10 g/L of PDB, 50 g/L of D-Fructose, 2 g/L of NH₄NO₃ and 1g/L of KH₂PO4. The contaminated gherkin plants are incubated at 17° C.and at 90% relative humidity.

Grading (% of efficacy) is carried out 4 to 5 days after thecontamination, in comparison with the control plants.

Under these conditions, high (at least 85%) protection is observed at adose of 500 ppm of active ingredient with the following compounds fromtable I:

TABLE I Example Efficacy 1 89 22 92

EXAMPLE J In Vivo Preventive Test on Pyricularia oryzae (Rice Blast)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Rice plants (“Koshihikari” variety), sown in starter cups on a 50/50peat soil pozzolana substrate and grown at 26° C., are treated at the 2leaf stage (10 cm height) by spraying with the active ingredientprepared as described above. Plants, used as controls, are treated withthe mixture of acetone/tween/DMSO/water not containing the activematerial.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Pyricularia oryzae spores (40 000 spores permL). The spores are collected from a 15-day-old culture and aresuspended in water containing 2.5 g/L of gelatin. The contaminated riceplants are incubated at 25° C. and at 80% relative humidity.

Grading (% of efficacy) is carried out 6 days after the contamination,in comparison with the control plants.

Under these conditions, high (at least 80%) to excellent (at least 90%)protection is observed at a dose of 500 ppm of active ingredient withthe following compounds from table J:

TABLE J Example Efficacy 45 83 46 92

EXAMPLE K In Vivo Preventive Test on Uromices appendiculatus (Bean Rust)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, and then diluted with water to obtain thedesired active material concentration.

Bean plants (“Saxa” variety), sown in starter cups on a 50/50 peat soilpozzolana substrate and grown at 24° C., are treated at the 2 leaf stage(9 cm height) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Uromyces appendiculatus spores (150 000 sporesper mL). The spores are collected from infected plants and are suspendedin water containing 2.5 mL/L of Tween 80 at 10%. The contaminated beanplants are incubated for 24 hours at 20° C. and at 100% relativehumidity, and then for 10 days at 20° C. and at 70-80% relativehumidity.

Grading (% of efficacy) is carried out 11 days after the contamination,in comparison with the control plants.

Under these conditions, high (at least 80%) to total protection isobserved at a dose of 500 ppm of active ingredient with the followingcompounds from table K:

TABLE K Example Efficacy 1 100 2 100 14 84 22 96

EXAMPLE L In Vivo Preventive Test on Leptosphaeria nodotrum (Wheat)

Solvent: 49 parts by weight of N,N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with apreparation of active compound at the stated rate of application. Oneday after this treatment, the plants are inoculated with an aqueousspore suspension of Leptosphaeria nodorum. The plants remain for 48hours in an incubation cabinet at 22° C. and a relative atmospherichumidity of 100%. Then the plants are placed in a greenhouse at atemperature of approximately 22° C. and a relative atmospheric humidityof approximately 90%.

The test is evaluated 7-9 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed.

Under these conditions, good (at least 70%) to excellent (at least 95%)protection is observed at a dose of 500 ppm of active ingredient withthe following compounds from table L:

TABLE L Example Efficacy 26 80 32 90 34 80 62 70 72 80 74 70 77 95 79 9092 80 93 80 99 70

1. A compound of formula (I)

wherein A represents a phenyl group that can be substituted by up tofive groups R or a carbo-linked, unsaturated or partially saturated,6-membered heterocyclyl group that can be substituted by up to fourgroups R; T represents O or S; n represents 0 or 1; B represents aphenyl ring that can be substituted by up to 5 groups X which can be thesame or different; a naphthyl ring that can be substituted by up to 7groups X which can be the same or different; a thienyl ring that can besubstituted by up to 3 groups X which can be the same or different; or abenzothiophenyl ring that can be substituted by up to 5 groups X whichcan be the same or different; X represents a halogen atom; nitro; cyano;isonitrile; hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl;formyloxy; formylamino; substituted or non-substituted(hydroxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl; substituted or non-substituted(benzyloxyimino)-C₁-C₈-alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl;carbamate; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted ornon-substituted C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl having 1 to 5halogen atoms; substituted or non-substituted C₂-C₈-alkynyl;C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfanyl;C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylamino; substituted ornon-substituted di-C₁-C₈-alkylamino; substituted or non-substitutedC₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms;substituted or non-substituted C₃-C₈-alkynyloxy;C₂-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₁-C₈-alkyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; substituted or non-substitutedC₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylcarbonyloxy;C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbonylamino;C₁-C₈-halogenoalkyl-carbonylamino having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkyloxycarbonyloxy;C₁-C₈-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; substituted or non-substitutedC₁-C₈-alkylaminocarbonyloxy; substituted or non-substituteddi-C₁-C₈-alkylaminocarbonyloxy; substituted or non-substitutedN—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or non-substitutedC₁-C₈-alkoxycarbamoyl; substituted or non-substitutedN—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that can be substituted byup to 6 groups Q which can be the same or different; C₁-C₈-arylalkylthat can be substituted by up to 6 groups Q which can be the same ordifferent; C₂-C₈-arylalkenyl that can be substituted by up to 6 groups Qwhich can be the same or different; C₂-C₈-arylalkynyl that can besubstituted by up to 6 groups Q which can be the same or different;aryloxy that can be substituted by up to 6 groups Q which can be thesame or different; arylsulfanyl that can be substituted by up to 6groups Q which can be the same or different; arylamino that can besubstituted by up to 6 groups Q which can be the same or different;C₁-C₈-arylalkyloxy that can be substituted by up to 6 groups Q which canbe the same or different; C₁-C₈-arylalkylsulfanyl that can besubstituted by up to 6 groups Q which can be the same or different; orC₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q whichcan be the same or different; or two substituent X together with theconsecutive carbon atoms to which they are linked can form a 5- or6-membered, saturated carbocycle or saturated heterocycle, which can besubstituted by up to four groups Q which can be the same or different;Z¹ and Z² independently represent a hydrogen atom; a halogen atom;cyano; substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkoxy; substituted or non-substituted C₁-C₈-alkylsulfanyl; orsubstituted or non-substituted C₁-C₈-alkoxycarbonyl; or Z¹ and Z² are aC₂-C₅-alkylene group that can be substituted by up to four C₁-C₈-alkylgroups; Z³ and Z⁴ independently represent a substituted ornon-substituted C₁-C₈-alkyl; Z⁵ and Z⁶ independently represent ahydrogen atom; a halogen atom; cyano; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxy; substituted ornon-substituted C₁-C₈-alkylsulfanyl; or substituted or non-substitutedC₁-C₈-alkoxycarbonyl; or Z⁵ and Z⁶ are a C₂-C₅-alkylene group that canbe substituted by up to four C₁-C₈-alkyl groups; Z⁷ represents ahydrogen atom; a formyl group; a substituted or non-substitutedC₁-C₈-alkyl; a substituted or non substituted C₁-C₈-alkoxy; anon-substituted C₃-C₇-cycloalkyl or a C₃-C₇-cycloalkyl substituted by upto 10 atoms or groups that can be the same or different and that can beselected in the list consisting of halogen atoms, cyano, C₁-C₈-alkyl,C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy comprising up to 9halogen atoms that can be the same or different, C₁-C₈-alkoxycarbonyl,C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that canbe the same or different, C₁-C₈-alkylaminocarbonyl anddi-C₁-C₈-alkylaminocarbonyl; Q independently represents a halogen atom;cyano; nitro; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl having 1 to 9 halogen atoms that can be the same ordifferent; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy having 1 to 9 halogen atoms that can be the same ordifferent; substituted or non-substituted C₁-C₈-alkylsulfanyl;C₁-C₈-halogenoalkylsulfanyl having 1 to 9 halogen atoms that can be thesame or different; substituted or non-substituted tri(C₁-C₈-alkyl)silyl;substituted or non-substituted tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl;substituted or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;substituted or non-substituted (benzyloxyimino)-C₁-C₈-alkyl; Rindependently represents hydrogen atom; halogen atom; nitro; cyano;hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; substituted ornon-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted ornon-substituted (benzyloxyimino)-C₁-C₈-alkyl; substituted ornon-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms; substituted or non-substituted C₂-C₈-alkenyl;C₂-C₈-halogenoalkenyl having 1 to 5 halogen atoms; substituted ornon-substituted C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1 to 5halogen atoms; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfonyl;C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylamino; substituted or non-substituteddi-C₁-C₈-alkylamino; substituted or non-substituted C₂-C₈-alkenyloxy;substituted or non-substituted C₃-C₈-alkynyloxy; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted tri(C₁-C₈-alkyl)silyl;substituted or non-substituted C₁-C₈-alkylcarbonyl;C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; phenoxy; phenylsulfanyl; phenylamino;benzyloxy; benzylsulfanyl; or benzylamino; as well as its salts,N-oxydes, metal complexes, metallic complexes and optically activeisomers.
 2. A compound according to claim 1 wherein A is selected in thelist consisting of: a carbocycle of formula (A¹)

wherein: R¹ represents a halogen atom; a hydroxy group; an amino group;a cyano group; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; R² to R⁵ that can be the same or differentrepresent a hydrogen atom; a halogen atom; a hydroxy group; an aminogroup; a cyano group; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; a heterocycle of formula (A²)

wherein: R⁶ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R⁷to R⁹ that can be the same or different represent a hydrogen atom; ahalogen atom; a hydroxy group; an amino group; a cyano group;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; a heterocycle of formula (A³)

wherein: R¹⁰ represents a halogen atom; a hydroxy group; an amino group,a cyano group; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; R¹¹ to R¹³ that can be the same or differentrepresent a hydrogen atom; a halogen atom; a hydroxy group; an aminogroup; a cyano group; substituted or non-substituted C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkoxy;C₁-C₅-halogenoalkoxy comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; a heterocycle of formula (A⁴)

wherein: R¹⁴ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R¹⁵to R¹⁷ that can be the same or different represent a hydrogen atom; ahalogen atom; a hydroxy group; an amino group; a cyano group;substituted or non-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 5 halogen atoms that can be the same or different;substituted or non-substituted C₁-C₅-alkylsulfanyl orC₁-C₅-halogenoalkylsulfanyl comprising up to 5 halogen atoms that can bethe same or different; a heterocycle of formula (A⁵)

wherein: R¹⁸ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R¹⁹and R²⁰ that can be the same or different represent a hydrogen atom; ahalogen atom; substituted or non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; a heterocycle of formula (A⁶)

wherein: R²¹ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R²²and R²³ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different; aheterocycle of formula (A⁷)

wherein: R²⁴ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R²⁵and R²⁶ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different; aheterocycle of formula (A⁸)

wherein: R²⁷ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R²⁸and R²⁹ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different; aheterocycle of formula (A⁹)

wherein: R³⁰ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R³¹and R³² that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different; aheterocycle of formula (A¹⁰)

wherein: R³³ represents a halogen atom; a cyano group; substituted ornon-substituted C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 5halogen atoms that can be the same or different; substituted ornon-substituted C₁-C₅-alkylsulfanyl or C₁-C₅-halogenoalkylsulfanylcomprising up to 5 halogen atoms that can be the same or different; R³⁴and R³⁵ that can be the same or different represent a hydrogen atom;substituted or non-substituted C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different;
 3. Acompound according to claim 2 wherein A is selected in the listconsisting of A¹; A³; A⁵ and A⁶.
 4. A compound according to claim 2wherein A represents A¹ wherein R¹ represents a halogen atom,substituted or non-substituted C₁-C₅-alkyl, C₁-C₅-halogenoalkylcomprising up to 5 halogen atoms that can be the same or different andR² to R⁵ represent a hydrogen atom.
 5. A compound according to claim 2wherein A represents A³ wherein R¹⁹ represents a halogen atom orC₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different and R¹¹ to R¹³ represent a hydrogen atom.
 6. Acompound according to claim 2 wherein A represents A⁵ wherein R¹⁸represents a halogen atom or C₁-C₅-halogenoalkyl comprising up to 5halogen atoms that can be the same or different and R¹⁹ and R²⁰represent a hydrogen atom.
 7. A compound according to claim 2 wherein Arepresents A⁶ wherein R²¹ represents a non-substituted C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different and R²² and R²³ represent a hydrogen atom.
 8. Acompound according to claim 1 wherein T represents O.
 9. A compoundaccording to claim 1 wherein B represents a substituted ornon-substituted phenyl ring or a substituted or non-substituted naphthylring.
 10. A compound according to claim 1 wherein X independentlyrepresents a halogen atom; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; substituted or non-substituted tri(C₁-C₈-alkyl)silyl;substituted or non-substituted C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different; orwherein two consecutive substituents X together with the phenyl ringform a substituted or non substituted 1,3-benzodioxolyl;1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl;1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.
 11. Acompound according to claim 1 wherein Z¹, Z², Z⁵ and Z⁶ independentlyrepresent a hydrogen atom, a substituted or non-substituted C₁-C₈-alkylor a substituted or non-substituted C₁-C₈-alkoxy.
 12. A compoundaccording to claim 1 wherein Z³ and Z⁴ independently represent anon-substituted C₁-C₈-alkyl.
 13. A compound according to claim 1 whereinZ⁷ represents a hydrogen atom, a non-substituted C₃-C₇ cycloalkyl or aC₃-C₇ cycloalkyl substituted by up to 10 groups or atoms that can be thesame or different and that can be selected in the list consisting ofhalogen atoms, C₁-C₈-alkyl, C₁-C₈-halogenoalkyl comprising up to 9halogen atoms that can be the same or different, C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different.
 14. A compound according to claim 1 wherein Rindependently represents a hydrogen atom; halogen atom; cyano;substituted or non-substituted C₁-C₈-alkylamino; substituted ornon-substituted di-C₁-C₈-alkylamino; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 5 halogen atoms that can be thesame or different; substituted or non-substituted C₁-C₈-alkylsulfanyl;amino; hydroxyl; nitro; substituted or non-substitutedC₁-C₈-alkoxycarbonyl; substituted or non-substituted C₂-C₈-alkynyloxy.15. A compound of formula (IIa)

wherein B, n, Z¹, Z², Z⁵ and Z⁶ are n represents 0 or 1; B represents aphenyl ring that can be substituted by up to 5 groups X which can be thesame or different; a naphthyl ring that can be substituted by up to 7groups X which can be the same or different; a thienyl ring that can besubstituted by up to 3 groups X which can be the same or different; or abenzothiophenyl ring that can be substituted by up to 5 groups X whichcan be the same or different; X represents a halogen atom; nitro; cyano;isonitrile hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl;formyloxy; formylamino; substituted or non-substituted(hydroxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl; substituted or non-substituted(C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl; substituted or non-substituted(benzyloxyimino)-C₁-C₈-alkyl; carboxy; carbamoyl; N-hydroxycarbamoyl;carbamate; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted ornon-substituted C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl having 1 to 5halogen atoms; substituted or non-substituted C₂-C₈-alkynyl;C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfanyl;C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfinyl; C₁-C₈-halogenoalkylsulfinyl having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylamino; substituted ornon-substituted di-C₁-C₈-alkylamino; substituted or non-substitutedC₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms;substituted or non-substituted C₃-C₈-alkynyloxy;C₂-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₁-C₈-alkyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; substituted or non-substitutedC₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylcarbonyloxy;C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbonylamino;C₁-C₈-halogenoalkyl-carbonylamino having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkyloxycarbonyloxy;C₁-C₈-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; substituted or non-substitutedC₁-C₈-alkylaminocarbonyloxy; substituted or non-substituteddi-C₁-C₈-alkylaminocarbonyloxy; substituted or non-substitutedN—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or non-substitutedC₁-C₈-alkoxycarbamoyl; substituted or non-substitutedN—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that can be substituted byup to 6 groups Q which can be the same or different; C₁-C₈-arylalkylthat can be substituted by up to 6 groups Q which can be the same ordifferent; C₂-C₈-arylalkenyl that can be substituted by up to 6 groups Qwhich can be the same or different; C₂-C₈-arylalkynyl that can besubstituted by up to 6 groups Q which can be the same or different;aryloxy that can be substituted by up to 6 groups Q which can be thesame or different; arylsulfanyl that can be substituted by up to 6groups Q which can be the same or different; arylamino that can besubstituted by up to 6 groups Q which can be the same or different;C₁-C₈-arylalkyloxy that can be substituted by up to 6 groups Q which canbe the same or different; C₁-C₈-arylalkylsulfanyl that can besubstituted by up to 6 groups Q which can be the same or different; orC₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q whichcan be the same or different; or two substituent X together with theconsecutive carbon atoms to which they are linked can form a 5- or6-membered, saturated carbocycle or saturated heterocycle, which can besubstituted by up to four groups Q which can be the same or different;Z¹ and Z² independently represent a hydrogen atom; a halogen atom;cyano; substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkoxy; substituted or non-substituted C₁-C₈-alkylsulfanyl; orsubstituted or non-substituted C₁-C₈-alkoxycarbonyl; or Z¹ and Z² are aC₂-C₅-alkylene group that can be substituted by up to four C₁-C₈-alkylgroups and; Z⁵ and Z⁶ independently represent a hydrogen atom; a halogenatom; cyano; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxy; substituted or non-substitutedC₁-C₈-alkylsulfanyl; or substituted or non-substitutedC₁-C₈-alkoxycarbonyl; or Z⁵ and Z⁶ are a C₂-C₅-alkylene group that canbe substituted by up to four C₁-C₈-alkyl groups; with the exclusion of:1-[dimethyl(phenyl)silyl]methanamine and its hydrochloride salt1-[dimethyl(phenyl)silyl]ethanamine and its hydrochloride salt(1R)-1-[dimethyl(phenyl)silyl]ethanamine1-[dimethyl(phenyl)silyl]propan-1-amine1-[dimethyl(phenyl)silyl]pentan-1-amine and its hydrochloride salt1-[dimethyl(phenyl)silyl]octan-1-amine1-[(4-methoxyphenyl)(dimethyl)silyl]methanamine1-[(3-fluorophenyl)(dimethyl)silyl]methanamine and its hydrochloridesalt 1-[(4-fluorophenyl)(dimethyl)silyl]methanamine1-[(4-chlorophenyl)(dimethyl)silyl]methanamine1-[benzyl(dimethyl)silyl]methanamine and its hydrochloride salt1-[(2-fluorobenzyl)(dimethyl)silyl]methanamine and its hydrochloridesalt 1-[(3-fluorobenzyl)(dimethyl)silyl]methanamine and itshydrochloride salt 1-[(4-fluorobenzyl)(dimethyl)silyl]methanamine andits hydrochloride salt 1-[(4-chlorobenzyl)(dimethyl)silyl]methanamine1-[(2,4-difluorobenzyl)(dimethyl)silyl]methanamine and its hydrochloridesalt 1-[(2,6-difluorobenzyl)(dimethyl)silyl]methanamine and itshydrochloride salt 1-[(3,4-difluorobenzyl)(dimethyl)silyl]methanamineand its hydrochloride salt1-[(3,5-difluorobenzyl)(dimethyl)silyl]methanamine1-[(3,4-dichlorobenzyl)(dimethyl)silyl]methanamine1-[dimethyl(2-thienylmethyl)silyl]methanamine.
 16. A compound of formula(IIb)

wherein n represents 0 or 1; B represents a phenyl ring that can besubstituted by up to 5 groups X which can be the same or different; anaphthyl ring that can be substituted by up to 7 groups X which can bethe same or different; a thienyl ring that can be substituted by up to 3groups X which can be the same or different; or a benzothiophenyl ringthat can be substituted by up to 5 groups X which can be the same ordifferent; X represents a halogen atom; nitro; cyano; isonitrile;hydroxy; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; formyl; formyloxyformylamino; substituted or non-substituted (hydroxyimino)-C₁-C₈-alkyl;substituted or non-substituted (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;substituted or non-substituted (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl;substituted or non-substituted (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl;substituted or non-substituted (benzyloxyimino)-C₁-C₈-alkyl; carboxy;carbamoyl; N-hydroxycarbamoyl; carbamate; substituted or non-substitutedC₁-C₈-alkyl; C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkenyl; C₂-C₈-halogenoalkenylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy having1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylsulfinyl;C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkylsulfonyl; C₁-C₈-halogenoalkylsulfonyl having1 to 5 halogen atoms; substituted or non-substituted C₁-C₈-alkylamino;substituted or non-substituted di-C₁-C₈-alkylamino; substituted ornon-substituted C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy having 1 to 5halogen atoms; substituted or non-substituted C₃-C₈-alkynyloxy;C₂-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms; substituted ornon-substituted C₃-C₇-cycloalkyl; C₃-C₇-halogenocycloalkyl having 1 to 5halogen atoms; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₁-C₈-alkyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkenyl; substituted or non-substituted(C₃-C₇-cycloalkyl)-C₂-C₈-alkynyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl; substituted or non-substitutedtri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; substituted or non-substitutedC₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogenatoms; substituted or non-substituted C₁-C₈-alkylcarbonyloxy;C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbonylamino;C₁-C₈-halogenoalkyl-carbonylamino having 1 to 5 halogen atoms;substituted or non-substituted C₁-C₈-alkoxycarbonyl;C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkyloxycarbonyloxyC₁-C₈-halogenoalkoxycarbonyloxy having 1 to 5 halogen atoms; substitutedor non-substituted C₁-C₈-alkylcarbamoyl; substituted or non-substituteddi-C₁-C₈-alkylcarbamoyl; substituted or non-substitutedC₁-C₈-alkylaminocarbonyloxy; substituted or non-substituteddi-C₁-C₈-alkylaminocarbonyloxy; substituted or non-substitutedN—(C₁-C₈-alkyl)hydroxy carbamoyl; substituted or non-substitutedC₁-C₈-alkoxycarbamoyl; substituted or non-substitutedN—(C₁-C₈-alkyl)-C₁-C₈-alkoxycarbamoyl; aryl that can be substituted byup to 6 groups Q which can be the same or different; C₁-C₈-arylalkylthat can be substituted by up to 6 groups Q which can be the same ordifferent; C₂-C₈-arylalkenyl that can be substituted by up to 6 groups Qwhich can be the same or different; C₂-C₈-arylalkynyl that can besubstituted by up to 6 groups Q which can be the same or different;aryloxy that can be substituted by up to 6 groups Q which can be thesame or different; arylsulfanyl that can be substituted by up to 6groups Q which can be the same or different; arylamino that can besubstituted by up to 6 groups Q which can be the same or different;C₁-C₈-arylalkyloxy that can be substituted by up to 6 groups Q which canbe the same or different; C₁-C₈-arylalkylsulfanyl that can besubstituted by up to 6 groups Q which can be the same or different; orC₁-C₈-arylalkylamino that can be substituted by up to 6 groups Q whichcan be the same or different; or two substituent X together with theconsecutive carbon atoms to which they are linked can form a 5- or6-membered, saturated carbocycle or saturated heterocycle, which can besubstituted by up to four groups Q which can be the same or different;Z¹ and Z² independently represent a hydrogen atom; a halogen atom;cyano; substituted or non-substituted C₁-C₈-alkyl; C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms; substituted or non-substitutedC₁-C₈-alkoxy; substituted or non-substituted C₁-C₈-alkylsulfanyl; orsubstituted or non-substituted C₁-C₈-alkoxycarbonyl; or Z¹ and Z² are aC₂-C₅-alkylene group that can be substituted by up to four C₁-C₈-alkylgroups; Z⁵ and Z⁶ independently represent a hydrogen atom; a halogenatom; cyano; substituted or non-substituted C₁-C₈-alkyl;C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms; substituted ornon-substituted C₁-C₈-alkoxy; substituted or non-substitutedC₁-C₈-alkylsulfanyl; or substituted or non-substitutedC₁-C₈-alkoxycarbonyl; or Z⁵ and Z⁶ are a C₂-C₅-alkylene group that canbe substituted by up to four C₁-C₈-alkyl groups; and Z⁷ represents acyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group,with the exclusion of:N-{[dimethyl-(phenyl)silyl]methyl}cyclohexanamine.
 17. A fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) according to claim 1 and an agriculturallyacceptable support, carrier or filler.
 18. A method for controllingphytopathogenic fungi of crops, characterized in that an agronomicallyeffective and substantially non-phytotoxic quantity of a compoundaccording to claim 1 is applied to the soil where plants grow or arecapable of growing, to the leaves and/or the fruit of plants or to theseeds of plants.
 19. A method for controlling phytopathogenic fungi ofcrops, characterized in that an agronomically effective andsubstantially non-phytotoxic quantity of a fungicide compositionaccording to claim 17 is applied to the soil where plants grow or arecapable of growing, to the leaves and/or the fruit of plants or to theseeds of plants.